[Bis-((S)-1-benzyloxymethyl-allyloxy)-phosphoryl]-diazo-acetic acid ethyl ester | 566915-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [Bis-((S)-1-benzyloxymethyl-allyloxy)-phosphoryl]-diazo-acetic acid ethyl ester
• CAS: 566915-10-4
• 化学式: C₂₆H₃₁N₂O₇P
• 分子量: 514.515
• InChiKey: YBAXXBYJKIAZOR-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  36.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  116.69
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [Bis-((S)-1-benzyloxymethyl-allyloxy)-phosphoryl]-diazo-acetic acid ethyl ester 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以63%的产率得到(4S)-4-benzyloxymethyl-2-((1S)-1-(benzyloxymethyl)allyloxy)-2-oxo-3-oxa-2λ⁵-phosphabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

  摘要：

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00081-8
• 作为产物：
  描述：

  [bis((1S)-1-(benzyloxymethyl)allyloxy)phosphoryl]acetic acid ethyl ester 在 对甲苯磺酰叠氮 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到[Bis-((S)-1-benzyloxymethyl-allyloxy)-phosphoryl]-diazo-acetic acid ethyl ester
  参考文献：
  名称：

  Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

  摘要：

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00081-8