(S)-diethyl(2-(1,3-dioxoisoindolin-2-yl)propanoyl)phosphonate | 151397-24-9

• 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: (S)-diethyl(2-(1,3-dioxoisoindolin-2-yl)propanoyl)phosphonate
• 英文别名: diethyl (S)-2-(phthalimido)propionylphosphonate；2-[(2S)-1-diethoxyphosphoryl-1-oxopropan-2-yl]isoindole-1,3-dione
• CAS: 151397-24-9
• 化学式: C₁₅H₁₈NO₆P
• 分子量: 339.285
• InChiKey: ACTSUWZOBNTNSU-JTQLQIEISA-N

物化性质

• 沸点：
  444.3±47.0 °C(predicted)
• 密度：
  1.332±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-diethyl(2-(1,3-dioxoisoindolin-2-yl)propanoyl)phosphonate 在 三正丁基氢锡 、 sodium cyanoborohydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 37.5h， 生成 (S)-diethyl 2-aminopropanephosphonate
  参考文献：
  名称：

  由 (S)-氨基酸不外消旋化制备旋光 (S)-2-氨基烷基膦酸

  摘要：

  光学活性 (S)-2-氨基丙基膦酸和 (S)-2-氨基-4-甲基戊基膦酸由市售的手性 α-氨基酸 [(S)-(+)-丙氨酸和 (S)-(+) -亮氨酸] 无外消旋化。

  DOI：

  10.1246/bcsj.63.2728
• 作为产物：
  描述：

  (S)-2-phthalimidopropionyl chloride 在 亚磷酸三乙酯 作用下， 反应 1.0h， 生成 (S)-diethyl(2-(1,3-dioxoisoindolin-2-yl)propanoyl)phosphonate
  参考文献：
  名称：

  由 (S)-氨基酸不外消旋化制备旋光 (S)-2-氨基烷基膦酸

  摘要：

  光学活性 (S)-2-氨基丙基膦酸和 (S)-2-氨基-4-甲基戊基膦酸由市售的手性 α-氨基酸 [(S)-(+)-丙氨酸和 (S)-(+) -亮氨酸] 无外消旋化。

  DOI：

  10.1246/bcsj.63.2728

文献信息

• Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers
  作者：Yan Cai、Haihong Ge、Weize Sun、Zhiwei Miao

  DOI：10.1055/s-0034-1380384

  日期：2015.6

  The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。
• Combined C–H functionalization/O–H insertion reaction to form tertiary β-alkoxy substituted β-aminophosphonates catalyzed by [Cu(MeCN)4]PF6
  作者：Yan Cai、Yuchen Lu、Chengbin Yu、Hairong Lyu、Zhiwei Miao

  DOI：10.1039/c3ob40941d

  日期：——

  The copper-catalyzed C–H functionalization/O–H insertion reaction of α-diazophosphonates with alcohols has been developed with iodine as an additive. In order to understand this reaction, we present here a possible mechanism for the combined reaction. This process provides straightforward access to tertiary β-alkoxy substituted β-aminophosphonate derivatives with moderate to good yields.

  已开发出以碘为添加剂的铜催化的α-二氮基膦酸酯与醇的C–H功能化/O–H插入反应。为了解释这一反应，我们在此提出了一个可能的联合作用机制。该过程可直接获得具有中到良好产率的叔β-醇氧基取代的β-氨基膦酸酯衍生物。
• Diastereoselective synthesis of β-amino-α-hydroxy phosphonates via oxazaborolidine catalyzed reduction of β-phthalimido-α-keto phosphonates
  作者：Achille Barco、Simonetta Benetti、Paola Bergamini、Carmela De Risi、Paolo Marchetti、Gian P. Pollini、Vinicio Zanirato

  DOI：10.1016/s0040-4039(99)01573-7

  日期：1999.10

  Reduction of β-phthalimido-α-keto phosphonates, obtained through an Arbuzov reaction between the appropriate acid chloride and triethyl phosphite, with boranes and oxazaborolidine as catalyst, afforded β-phthalimido-α-hydroxy phosphonates in good yields and high diastereoselectivity. Deprotection of the amino group gave the title compounds.

  通过适当的酰氯和亚磷酸三乙酯之间的Arbuzov反应，以硼烷和恶唑硼烷为催化剂，还原β-邻苯二甲酰亚胺基-α-羟基膦酸酯，可提供高收率和高非对映选择性的β-邻苯二甲酰亚胺基-α-羟基膦酸酯。氨基的脱保护得到标题化合物。
• 1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
  作者：Zhiwei Miao、Haihong Ge、Shuang Liu、Yan Cai、Yuchao Sun

  DOI：10.1055/s-0035-1560373

  日期：——

  The regiospecific and stereoselective 1,2-migration reaction of dialkyl alpha-diazophosphonates for the synthesis of beta-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)(4)PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to beta-amino (E)-enylphosphonates in moderate to good yields.
• Unexpected Stereoselective Synthesis of (<i>Z</i>)-β-Alkenyl Substituted β-Amino Phosphonates through β,γ-Dihydrogen Shift Reaction Catalyzed by a Copper(I) Complex and Iodine [Cu(MeCN)₄]PF₆/I₂
  作者：Yan Cai、Hairong Lyu、Chengbin Yu、Zhiwei Miao

  DOI：10.1002/adsc.201300838

  日期：2014.2.10

  AbstractA series of dialkyl α‐diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN)4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl α‐diazophosphonates gave a mixture of β,γ‐dihydrogen shift and 1,2‐hydride migration products and afforded β‐alkenyl‐substituted β‐amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.magnified image