Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester methyl ester | 131042-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester methyl ester
• 英文别名: (1,3-dioxoisoindol-2-yl) methyl carbonate
• CAS: 131042-51-8
• 化学式: C₁₀H₇NO₅
• 分子量: 221.169
• InChiKey: UPISJTUDRGJQRS-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C(Solv: ethanol (64-17-5))
• 沸点：
  341.0±25.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  sodium N-hydroxyphthalimide 、 氯甲酸甲酯 以 水 、 丙酮 为溶剂， 反应 16.0h， 以74%的产率得到Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester methyl ester
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of imidooxy derivatives

  摘要：

  Previous results of anticonvulsant activity in several imidooxy carboxylates related to (aminooxy)acetic acid in young chicks, prompted an in-depth reinvestigation of these analogues in mice. A series of 22 succinimidooxy, phthalimidooxy, and naphthalimidooxy carboxylates were synthesized and evaluated for anticonvulsant activity by the National Institute of Neurological and Communicative Disorders and Stroke (NINCDS). Methyl (succinimidooxy)acetate (2d), ethyl (succinimidooxy)acetate (2e), methyl (phthalimidooxy)acetate (3d), ethyl (phthalimidooxy)acetate (3e), and ethyl 2-(phthalimidooxy)propionate (3g), which were initially found to be active as anticonvulsants in young chicks were uniformly inactive in the Phase I seizure tests involving maximal electroshock (MES), pentylenetetrazol (scMet), or neurologic toxicity toxicity (Tox). Several newer analogues, ethyl (succinimidooxy)formate (2c) and methyl 3-(phthalimidooxy)-2-methylacrylate (4h) were found to be active in the scMet (3a) or both (4h) evaluations. Most interesting was the anticonvulsant results of N-(benzyloxy)-2-azaspiro[4.4]nonane-1,3-dione (5b), which displayed anti-MES activity and a protective index (TD50/ED50) of > 4.5.

  DOI：

  10.1021/jm00105a059

文献信息

• Degradable polymer article
  申请人：Sala Massimiliano

  公开号：US20090286060A1

  公开（公告）日：2009-11-19

  A polymer article having accelerated degradability triggered by light and/or heat and/or humidity and made of a composition containing (A) a natural and/or a synthetic polymer and (B) a degradation accelerator of the formula (I), wherein n is 1, 2 or 4; X is >C=0, >S(O) 2 or >C(X 1 )(X 2 ); X 1 and X 2 independently of one another are hydrogen, C 1 -C 20 alkyl, C 3 -C 12 cycloalkyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; or phenyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; Y is C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 3 -C 12 cycloalkyl unsubstituted or substituted by 1, 2 or 3 C 1 C 4 alkyl; C 5 -C 12 cycloalkenyl unsubstituted or substituted by 1, 2 or 3 C 1 C 4 alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms, C 7 -C 4 phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; diphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; triphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; C 2 -C 30 acyl, —COOY 0 , C 1 -C 30 sulfonyl, —Si(Y 1 ) 3 or —Si(OY 2 ) 3 ; Y 0 , Y 1 and Y 2 independently of one another are hydrogen, C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 12 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; or C 7 -C 9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; and Z is an organic radical; with the provisos that (1) when Y is C 1 -C 30 alkyl, C 2 -C 30 alkenyl or C 1 -C 30 sulfonyl, component (A) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer; and (2) when n is 2 or 4 and, at the same time, component (A) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer, Y is additionally hydrogen.

  一种聚合物制品，其可被光、热和/或湿度加速降解，由含有（A）天然和/或合成聚合物和（B）式（I）的降解加速剂的组合物制成，其中n为1、2或4；X为>C=0、>S（O）2或>C（X1）（X2）；X1和X2分别独立地为氢、C1-C20烷基、未取代或取代1、2或3个C1-C4烷基的C3-C12环烷基；或未取代或取代1、2或3个C1-C4烷基的苯基；Y为C1-C30烷基、C2-C30烯基、未取代或取代1、2或3个C1C4烷基的C3-C12环烷基；未取代或取代1、2或3个C1C4烷基的C5-C12环烯基；具有6到10个碳原子的双环或三环烃基、未取代或取代1、2或3个C1-C4烷基的C7-C4苯基烷基；未取代或取代1、2或3个C1-C4烷基的二苯甲基；未取代或取代1、2或3个C1-C4烷基的三苯甲基；C2-C30酰基，—COOY0，C1-C30磺酰基，—Si（Y1）3或—Si（OY2）3；Y0、Y1和Y2分别独立地为氢、C1-C18烷基、C3-C18烯基、未取代或取代1、2或3个C1-C4烷基的C3-C12环烷基；未取代或取代1、2或3个C1-C4烷基的苯基；或未取代或取代1、2或3个C1-C4烷基的C7-C9苯基烷基；Z为有机基；但前提是（1）当Y为C1-C30烷基、C2-C30烯基或C1-C30磺酰基时，组分（A）为聚烯烃同聚物或共聚物或聚烯烃同聚物或共聚物与其他合成聚合物的混合物；（2）当n为2或4且同时组分（A）为聚烯烃同聚物或共聚物或聚烯烃同聚物或共聚物与其他合成聚合物的混合物时，Y还额外为氢。
• EDAFIOGHO, IVAN O.;SCOTT, K. R.;MOORE, JACQUELINE A.;FARRAR, VIDA A.;NICH+, J. MED. CHEM., 34,(1991) N, C. 387-392
  作者：EDAFIOGHO, IVAN O.、SCOTT, K. R.、MOORE, JACQUELINE A.、FARRAR, VIDA A.、NICH+

  DOI：——

  日期：——
• [EN] A DEGRADABLE POLYMER ARTICLE<br/>[FR] ARTICLE EN POLYMÈRE DÉGRADABLE
  申请人：CIBA SC HOLDING AG

  公开号：WO2007028731A1

  公开（公告）日：2007-03-15

  [EN] A polymer article having accelerated degradability triggered by light and/or heat and/or humidity and made of a composition containing (A) a natural and/or a synthetic polymer and (B) a degradation accelerator of the formula (I), wherein n is 1, 2 or 4; X is >C=0, >S(O)₂ or >C(X₁)(X₂); X₁ and X₂ independently of one another are hydrogen, C₁-C₂₀alkyl, C₃-C₁₂cycloalkyl unsubstituted or substituted by 1, 2 or 3 C₁-C₄alkyl; or phenyl unsubstituted or substituted by 1 , 2 or 3 C₁-C₄alkyl; Y is C_i-C₃₀alkyl, C₂-C₃₀alkenyl, C₃-C₁₂cycloalkyl unsubstituted or substituted by 1 , 2 or 3 C₁C₄alkyl; C₅-C₁₂cycloalkenyl unsubstituted or substituted by 1, 2 or 3 C₁C₄alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms, C₇-C₄phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; diphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; triphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; C₂-C₃₀acyl, -COOY₀, C₁-C₃₀sulfonyl, -Si(Y₁)₃ or -Si(OY₂)₃; Y₀, Y₁ and Y₂ independently of one another are hydrogen, C₁-C₁₈alkyl, C₃-C-₁₈alkenyl, C₃-C₁₂cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C₁-C₄alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C₁-C₄alkyl; or C₇-C₉phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; and Z is an organic radical; with the provisos that (1) when Y is C₁-C₃₀alkyl, C₂-C₃₀alkenyl or C₁-C₃₀sulfonyl, component (A) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer; and (2) when n is 2 or 4 and, at the same time, component (A) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer, Y is additionally hydrogen.
  [FR] Article en polymère, selon l'invention, ayant une dégradabilité accélérée déclenchée par la lumière et/ou la chaleur et/ou l'humidité et constitué d'une composition contenant (A) un polymère naturel et/ou un polymère synthétique et (B) un accélérateur de dégradation de formule (I), dans laquelle n est 1, 2 ou 4 ; X est >C=0, >S(O)₂ ou >C(X₁)(X₂) ; X₁ et X₂ sont chacun indépendamment l'un de l'autre un hydrogène, un alkyle en C₁-C₂₀, un cycloalkyle en C₃-C₁₂ non substitué ou substitué par 1, 2 ou 3 alkyles en C₁-C₄ ; ou un phényle non substitué ou substitué par 1, 2 ou 3 alkyles en C₁-C₄ ; Y est un alkyle en C₁-C₃₀, un alcényle en C₂-C₃₀, un cycloalkyle en C₃-C₁₂ non substitué ou substitué par 1, 2 ou 3 alkyles en C₁-C₄ ; un cycloalcényle en C₅-C₁₂ non substitué ou substitué par 1, 2 ou 3 alkyles en C₁-C₄ ; un groupe hydrocarboné bicyclique ou tricyclique ayant 6 à 10 atomes de carbone, un phénylalkyle en C₇-C₄ non substitué ou substitué sur le phényle par 1, 2 ou 3 alkyles en C₁-C₄; un diphénylméthyle non substitué ou substitué sur le phényle par 1, 2 ou 3 alkyles en C₁-C₄ ; un triphénylméthyle non substitué ou substitué sur le phényle par 1, 2 ou 3 alkyles en C₁-C₄ ; un acyle en C₂-C₃₀, -COOY₀, un sulfonyle en C₁-C₃₀, -Si(Y₁)₃ ou -Si(OY₂)₃ ; Y₀, Y₁ et Y₂ sont chacun indépendamment les uns des autres un hydrogène, un alkyle en C₁-C₁₈, un alcényle en C₃-C₁₈, un cycloalkyle en C₃-C₁₂ qui est non substitué ou substitué par 1, 2 ou 3 alkyles en C₁-C₄ ; un phényle qui est non substitué ou substitué par 1, 2 ou 3 alkyles en C₁-C₄ ; ou un phénylalkyle en C₇-C₉ qui est non substitué ou substitué sur le phényle par 1, 2 ou 3 alkyles en C₁-C₄; et Z est un radical organique ; à condition que (1) lorsque Y est un alkyle en C₁-C₃₀, un alcényle en C₂-C₃₀ ou un sulfonyle en C₁-C₃₀, le composant (A) soit un homopolymère ou copolymère de type polyoléfine ou un mélange d'un homopolymère ou copolymère de type polyoléfine avec un autre polymère synthétique ; et (2) lorsque n est 2 ou 4 et qu'en même temps le composant (A) est un homopolymère ou copolymère de type polyoléfine ou un mélange d'un homopolymère ou copolymère de type polyoléfine avec un autre polymère synthétique, Y soit en plus un hydrogène.
• Synthesis and anticonvulsant activity of imidooxy derivatives
  作者：Ivan O. Edafiogho、K. R. Scott、Jacqueline A. Moore、Vida A. Farrar、Jesse M. Nicholson

  DOI：10.1021/jm00105a059

  日期：1991.1

  Previous results of anticonvulsant activity in several imidooxy carboxylates related to (aminooxy)acetic acid in young chicks, prompted an in-depth reinvestigation of these analogues in mice. A series of 22 succinimidooxy, phthalimidooxy, and naphthalimidooxy carboxylates were synthesized and evaluated for anticonvulsant activity by the National Institute of Neurological and Communicative Disorders and Stroke (NINCDS). Methyl (succinimidooxy)acetate (2d), ethyl (succinimidooxy)acetate (2e), methyl (phthalimidooxy)acetate (3d), ethyl (phthalimidooxy)acetate (3e), and ethyl 2-(phthalimidooxy)propionate (3g), which were initially found to be active as anticonvulsants in young chicks were uniformly inactive in the Phase I seizure tests involving maximal electroshock (MES), pentylenetetrazol (scMet), or neurologic toxicity toxicity (Tox). Several newer analogues, ethyl (succinimidooxy)formate (2c) and methyl 3-(phthalimidooxy)-2-methylacrylate (4h) were found to be active in the scMet (3a) or both (4h) evaluations. Most interesting was the anticonvulsant results of N-(benzyloxy)-2-azaspiro[4.4]nonane-1,3-dione (5b), which displayed anti-MES activity and a protective index (TD50/ED50) of > 4.5.