(4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1λ⁵-phosphatricyclo<6.3.0.0^1,5>undecane | 128471-02-3

• 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: (4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1λ⁵-phosphatricyclo<6.3.0.0^1,5>undecane
• 英文别名: (4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1-λ⁵-phosphatricyclo[6.3.0.0^1,5]undecane；(4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1λ⁵-phosphatricyclo[6.3.0.0^1,5]undecane；(4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1λ5-phosphatricyclo[6.3.0.01,5]undecane
• CAS: 128471-02-3
• 化学式: C₂₀H₂₅N₂O₂P
• 分子量: 356.404
• InChiKey: RYEGOVOIPKOJFZ-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.94
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二甲基二硫 、 (4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1λ⁵-phosphatricyclo<6.3.0.0^1,5>undecane 以 甲苯 为溶剂， 反应 44.0h， 以90%的产率得到(4S,9S)-4,9-Dibenzyl-1-methylsulfanyl-2,11-dioxa-5,8-diaza-1λ⁵-phospha-tricyclo[6.3.0.0^1,5]undecane
  参考文献：
  名称：

  Alkylthiylation of triquinphosphoranes by disulfides: an entry to chiral thiatriquinphosphoranes

  摘要：

  Triquinphosphoranes 1 undergo alkylthiylation reactions, even in the dark, with methyl and n-butyl disulfides to give the corresponding thiaphosphoranes with high yields. Chiral triquinphosphorane 2, by this reaction, gives rise to chiral thiatriquinphosphorane 4. The reaction with t-BuSSBu-t preferably gave the thiophosphoramide. An increased reactivity was observed when the experiments were conducted under UV irradiation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00338-5
• 作为产物：
  描述：

  (2S)-2-[(2-{[(2S)-1-羟基-3-苯基丙烷-2-基]氨基}乙基)氨基]-3-苯基丙烷-1-醇 、 三(二甲胺基)膦 以 甲苯 为溶剂， 反应 1.0h， 以80%的产率得到(4S,9S)-4,9-dibenzyl-2,11-dioxa-5,8-diaza-1λ⁵-phosphatricyclo<6.3.0.0^1,5>undecane
  参考文献：
  名称：

  Vannoorcnberghe, Yves; Buono, Gerard, Journal of the American Chemical Society, 1990, vol. 112, # 16, p. 6142 - 6143

  摘要：

  DOI：

文献信息

• Asymmetric addition of chiral triquinphosphoranes on activated carbonyl compounds
  作者：Caroline Marchi、Gérard Buono

  DOI：10.1016/s0040-4039(99)02023-7

  日期：1999.12

  trifluoroacetophenone, ketopantolactone and aromatic aldehydes affording pairs of hydroxyphosphoranes diastereomers with a diastereoselectivity up to 90% depending on the nature of the electrophile. In the case of ketopantolactone, hydroxyphosphorane diastereomers are quantitatively converted to alkoxyphosphoranes with a decreasing of diastereomeric excesses. The major alkoxyphosphorane diastereomer exhibits a

  手性三喹磷光烷与三氟苯乙酮，酮戊内酯和芳族醛反应，得到对羟基磷光烷非对映异构体，其对映选择性高达90％，这取决于亲电试剂的性质。在酮基内酯的情况下，随着非对映异构体过量的减少，羟基磷烷非对映异构体被定量地转化为烷氧基膦酸酯。通过X射线衍射分析确定，主要的烷氧基磷烷非对映异构体显示出紧密的SP结构。
• First totally diastereoselective opening of chiral triquinphosphoranes. A new access to enantiopure oxazaphospholidines
  作者：Caroline Marchi、Guillaume Delapierre、Frédéric Fotiadu、Gérard Buono

  DOI：10.1039/b005884j

  日期：——

  Asymmetric addition of isocyanate compounds on chiral triquinphosphoranes, tricyclic hydridophosphoranes, led by a total diastereoselective opening of the diazaphospholidine ring. This provides chiral bicyclic oxazaphospholidines in which an eight-membered ring is fused to the oxazaphospholidine ring by the P–N bond.

  异氰酸酯化合物与手性三喹啉磷烷、三环氢化物磷烷的不对称加成，导致重氮膦环的完全非对映选择性打开。这样就得到了手性双环噁唑磷烷，其中一个八元环通过 P-N 键与噁唑磷啶环融合。