(1,1-dibromopropyl)triphenylphosphonium bromide | 66070-36-8

• 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: (1,1-dibromopropyl)triphenylphosphonium bromide
• 英文别名: 1,1-Dibromopropyl(triphenyl)phosphanium;bromide
• CAS: 66070-36-8
• 化学式: Br*C₂₁H₂₀Br₂P
• 分子量: 543.076
• InChiKey: IXWCVCGAZGGMCH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1,1-dibromopropyl)triphenylphosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (1-Bromo-propylidene)-triphenyl-λ⁵-phosphane
  参考文献：
  名称：

  Synthese deuterierter und brom-substituierter olefine aus dialkylboryl-alkylidentriphenylphosphoranen

  摘要：

  DOI：

  10.1016/s0040-4039(00)84430-5
• 作为产物：
  描述：

  (1-Dicyclopentylboranyl-propylidene)-triphenyl-λ⁵-phosphane 在 溴 作用下， 以93%的产率得到(1,1-dibromopropyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Synthese deuterierter und brom-substituierter olefine aus dialkylboryl-alkylidentriphenylphosphoranen

  摘要：

  DOI：

  10.1016/s0040-4039(00)84430-5

文献信息

• Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin
  作者：Daisuke Matsumura、Toshimasa Takarabe、Takumi Toda、Takashi Hayamizu、Kiyoto Sawamura、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1016/j.tet.2011.04.006

  日期：2011.9

  The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels–Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton

  天然（+）-吡啶甲酸A和（+）-zygomphmphic酸（聚酮化合物来源的新的细胞毒性海洋天然产物）的总合成已首次完成。这些合成是通过功能化的（E，E，E）-2,7,9-十二碳六烯衍生物的高度立体选择性和高产率的分子内Diels-Alder反应实现的，以构建核心的四氢茚满-2-一骨架。还合成了（+）-吡啶甲酸A的立体异构体，即（2 R，5 S，6 R）-异构体。描述了这些全部合成的细节。
• Stereoselective Construction of 2,7-Disubstituted <i>fused</i>-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (−)-Aplysiallene and Their Derivatives
  作者：Maki Yamakawa、Takeshi Kurachi、Yusuke Yoshikawa、Mitsuhiro Arisawa、Yuichiro Okino、Kuniaki Suzuki、Hiromichi Fujioka

  DOI：10.1021/acs.joc.5b01882

  日期：2015.10.16

  A series of trans/trans and cis/cis fused-bis tetrahydrofuran compounds have been obtained stereoselectively in high yields via a one-pot operation involving the intramolecular haloetherification of (Z,Z)-diene diol 19a and (E,E)-diene disilylether 19d, respectively. This method was subsequently applied to the biomimetic-type synthesis of (+/-)- and (-)-aplysiallene. The inhibitory activities of these compounds and their bromodiene isomers toward Na+/K+ ATPase were determined in vitro, and gave IC50 values of approximately 15 mu M in all cases.
• Total Synthesis of (-)-Dactylynes
  作者：Akio Murai、Lian-xun Gao

  DOI：10.3987/com-95-s84

  日期：——
• A new stereoselective route to trisubstituted bromo olefins utilizing .alpha.-bromoalkylides produced by halogen-metal exchange
  作者：Roger H. Smithers

  DOI：10.1021/jo00408a019

  日期：1978.7
• Total synthesis of (+)-spiculoic acid A
  作者：Daisuke Matsumura、Takumi Toda、Takashi Hayamizu、Kiyoto Sawamura、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2009.02.101

  日期：2009.7

  The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereciselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton. (C) 2009 Elsevier Ltd. All rights reserved.