5(S)-hydroxy-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one | 72937-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5(S)-hydroxy-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one
• 英文别名: (-)-3-hydroxy-3a,4,7,7a-tetrahydro-4,5-methano-(3H)-isobenzofuran-1-one；(3S,3aS,4R,7S,7aR)3-hydroxy-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran-1-one；(1S,2R,5S,6S,7R)-5-hydroxy-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 72937-71-4
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: QJQKWWRFMPGUIQ-YMVPXFTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5(S)-hydroxy-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one 在 吡啶 、 草酰氯 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 31.0h， 生成
  参考文献：
  名称：

  吲哚生物碱的合成方法。使用异常温和的逆狄尔斯-阿尔德反应合成五环去乙基蜘蛛精类生物碱的对映体特异性合成

  摘要：

  Lapyryse de l'adduit (A) du chlorure de l'acidevinyl-3 norbornene-5carboxylique-2 et du methoxycarbonyl-1methyl-2 phenylthio-1'ethyliminomethyl-3 indole donne un produit retro-Diels-Alder (B) , l'六氢甲氧基羰基-7苯硫基-2'乙基-1吡啶并[3,2-c]咔唑酮-2；A et B sont convertis separement en methoxycarbonyl-1 tetrahydro-2,3,6,7 phenylthio-11p desethyl-20 aspidospermidinone-8

  DOI：

  10.1021/ja00262a006
• 作为产物：
  描述：

  [(1R,2S,3R,6R,7S)-5-oxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-yl] acetate 在 4 A molecular sieve 、 正丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以98%的产率得到5(S)-hydroxy-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one
  参考文献：
  名称：

  Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.0^2,6]dec-8-en-3-ones:  A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity

  摘要：

  Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.

  DOI：

  10.1021/jo9610220

文献信息

• Substituted lactones of amino acids
  申请人：Roussel Uclaf

  公开号：US04513139A1

  公开（公告）日：1985-04-23

  Novel substituted lactones of amino acids in all their possible stereoisomeric forms or mixtures thereof of the formula ##STR1## wherein A is a hydrocarbon chain of 1 to 10 chain members containing one or more heteroatoms and one or more unsaturations and the chain members being a mono- or polycyclic system or comprises a system of spiro or endo type and may contain one or more chiral atoms or the lactone copula can present a supplementary chirality due to the asymetric spatial configuration of the molecule make up and R is selected from the group consisting of ##STR2## wherein Z is the organic remainder of an amino acid of the formula ##STR3## Y is derived from a primary, secondary or tertiary alcohol of the formula Y--OH and B is the remainder of a heterocyclic amino acid of 3 to 6 carbon atoms of the formula ##STR4## and their preparation and their use for the resolution of amino acids.

  这是一段化学领域的描述，以下是翻译结果： 该小说用所有可能的立体异构体或混合物替代了氨基酸内的内酯，其化学式为##STR1## 其中，A是由1至10个链成员组成的碳氢链，其中包含一个或多个杂原子和一个或多个不饱和度，链成员是单环或多环系统，或包括一个螺旋或内向型系统，可能包含一个或多个手性原子，或者内酯偶合物可以由分子组成的不对称空间构型呈现额外的手性，R被选自下列组：##STR2## 其中，Z是氨基酸的有机残基，其化学式为##STR3## Y源自于化学式为Y-OH的一级、二级或三级醇，B是由3至6个碳原子组成的杂环氨基酸的余数，其化学式为##STR4## 这些化合物的制备和用于分离氨基酸的用途。
• Process for resolving amino acids using substituted lactones
  申请人：Roussel Uclaf

  公开号：US05136050A1

  公开（公告）日：1992-08-04

  Novel substituted lactones of amino acids in all their possible stereoisomeric forms or mixtures thereof of the formula ##STR1## wherein A is a hydrocarbon chain of 1 to 10 chain members containing one or more heteroatoms and one or more unsaturations and the chain members being a mono- or polycyclic system or comprises a system of spiro or endo type and may contain one or more chiral atoms or the lactone copula can present a supplementary chirality due to the asymetric spatial configuration of the molecule make up and R is selected from the group consisting of ##STR2## wherein Z is the organic remainder of an amino acid of the formula ##STR3## Y is derived from a primary, secondary or tertiary alcohol of the formula Y-OH and B is the remainder of a heterocycle amino acid of 3 to 6 carbon atoms of the formula ##STR4## and their preparation and their use for the resolution of amino acids.

  该发明涉及一种所有可能的立体异构体或其混合物的氨基酸代替内酯的小说化合物，其化学式为##STR1##其中，A是一个含有一个或多个杂原子和一个或多个不饱和度的1到10个链成员的碳氢链，链成员是一个单环或多环系统或包含一个螺旋或内型系统，可以包含一个或多个手性原子，或者内酯联合物可以由分子构成的不对称空间构型而呈现出补充手性，而R是选择自以下组：##STR2##其中Z是氨基酸的有机残基，其化学式为##STR3##Y是从化学式为Y-OH的一级、二级或三级醇中得到的，而B是3到6个碳原子的杂环氨基酸的余数，其化学式为##STR4##以及它们的制备和它们用于分辨氨基酸。
• US4513139A
  申请人：——

  公开号：US4513139A

  公开（公告）日：1985-04-23
• Methods for indole alkaloid synthesis. Enantiospecific synthesis of pentacyclic deethylaspidosperma-type alkaloids using an exceptionally mild retro-Diels-Alder reaction
  作者：Philip. Magnus、Peter M. Cairns

  DOI：10.1021/ja00262a006

  日期：1986.1

  La pyrolyse de l'adduit (A) du chlorure de l'acide vinyl-3 norbornene-5carboxylique-2 et du methoxycarbonyl-1 methyl-2 phenylthio-1' ethyliminomethyl-3 indole donne un produit retro-Diels-Alder (B), l'hexahydro methoxycarbonyl-7 phenylthio-2' ethyl-1 pyrido [3,2-c] carbazolone-2; A et B sont convertis separement en methoxycarbonyl-1 tetrahydro-2,3,6,7 phenylthio-11p desethyl-20 aspidospermidinone-8

  Lapyryse de l'adduit (A) du chlorure de l'acidevinyl-3 norbornene-5carboxylique-2 et du methoxycarbonyl-1methyl-2 phenylthio-1'ethyliminomethyl-3 indole donne un produit retro-Diels-Alder (B) , l'六氢甲氧基羰基-7苯硫基-2'乙基-1吡啶并[3,2-c]咔唑酮-2；A et B sont convertis separement en methoxycarbonyl-1 tetrahydro-2,3,6,7 phenylthio-11p desethyl-20 aspidospermidinone-8
• Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-<i>endo-</i>tricyclo[5.2.1.0^2,6]dec-8-en-3-ones:  A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity
  作者：Jan Willem J. F. Thuring、Gerard H. L. Nefkens、Margreth A. Wegman、Antonius J. H. Klunder、Binne Zwanenburg

  DOI：10.1021/jo9610220

  日期：1996.1.1

  Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.