(Z)-1-Cyclohexyl-3-(tributylstannyl)hept-2-enol | 130708-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-Cyclohexyl-3-(tributylstannyl)hept-2-enol
• 英文别名: (Z)-C6H11CH(OH)CHC(Bu)SnBu3
• CAS: 130708-13-3
• 化学式: C₂₅H₅₀OSn
• 分子量: 485.381
• InChiKey: JAUJPZIHDXMVOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-Cyclohexyl-3-(tributylstannyl)hept-2-enol 在 Rh(norbornadiene)(bis(diphenylphosphino)butane)(+)BF4(-) 氢气 作用下， 以 二氯甲烷 为溶剂， 以0%的产率得到
  参考文献：
  名称：

  Lautens, Mark; Zhang, ChunHao; Crudden, Cathleen M., Angewandte Chemie, 1992, vol. 104, # 2, p. 237 - 239

  摘要：

  DOI：
• 作为产物：
  描述：

  1-环己基庚-2-炔-1-醇 、 三丁基氯化锡 、 四氢呋喃 生成 (Z)-1-Cyclohexyl-3-(tributylstannyl)hept-2-enol
  参考文献：
  名称：

  LAUTENS, MARK;HUBOUX, ALEXANDRE H., TETRAHEDRON LETT., 31,(1990) N2, C. 3105-3108

  摘要：

  DOI：

文献信息

• Exploring the reactivity of alkenes bearing silicon and/or tin in the hydroxyl-directed hydrogenation. A diastereoselective synthesis of heterobimetallic compounds
  作者：Mark Lautens、C. H. Zhang、Betty Jane Goh、Cathleen M. Crudden、Marc J. A. Johnson

  DOI：10.1021/jo00100a023

  日期：1994.10

  The hydroxyl-directed hydrogenation of (E)- and (Z)-gamma-hydroxy vinylstannanes and silanes has been studied in the presence of (dppb)Rh(NBD)BF4 (1). Efficient routes to gamma-hydroxy stannanes and silanes have been developed. Diastereoselectivities from 60 to >500:1 were observed. A significant difference in reaction rate and pathway was observed between the (E)- and (Z)-vinylstannanes. We observed a reductive destannation process for the (Z)-stannanes which was influenced by the size of the R group. Competition studies were carried out to determine if steric or electronic effects were responsible for the reactivity patterns observed.
• Diastereoselectivity in the Cyclopropanation of 3,3-Bimetallic Allylic Alcohols. Preparation of Diastereomeric Cyclopropyl Carbinols via a Simple Oxidation-Reduction Sequence
  作者：Mark Lautens、Patrick H. M. Delanghe

  DOI：10.1021/jo00113a031

  日期：1995.4

  A highly diastereoselective cyclopropanation of allylic alcohols, containing a silyl and/or stannyl group using samarium/dihalomethane, provides a variety of bimetallic cyclopropane carbinols in good yield. A comparison with the more traditional Simmons-Smith conditions and its variants is made. The diastereoselectivity varies from 1:10 to >50:1 and depends on the substituents on the carbinol side chain (R-group) and on the substituents on the alkene portion of the allylic alcohol. Excellent diastereoselectivity (>50:1) was always obtained whenever a eis-substituent was present. Moreover, the minor diastereomer from the cyclopropanation can easily be obtained via a simple oxidation of the major cyclopropyl carbinol, followed by a selective reduction of the corresponding cyclopropyl ketone. Using LiAlH4 at 0 degrees C, facial selectivities of 15 to 20:1 are obtained for this reduction, while slightly higher selectivities up to (29:1) can be obtained using DIBAL-H. The combination of the cyclopropanation and oxidation/selective reduction sequence provides access to both diastereomeric bimetallic cyclopropanes.
• LAUTENS, MARK;HUBOUX, ALEXANDRE H., TETRAHEDRON LETT., 31,(1990) N2, C. 3105-3108
  作者：LAUTENS, MARK、HUBOUX, ALEXANDRE H.

  DOI：——

  日期：——
• LAUTENS, MARK;HUBOUX, ALEXANDRE H.;CHIN, BAIN;DOWNER, JULIA, TETRAHEDRON LETT., 31,(1990) N1, C. 5829-5832
  作者：LAUTENS, MARK、HUBOUX, ALEXANDRE H.、CHIN, BAIN、DOWNER, JULIA

  DOI：——

  日期：——
• Lautens, Mark; Zhang, ChunHao; Crudden, Cathleen M., Angewandte Chemie, 1992, vol. 104, # 2, p. 237 - 239
  作者：Lautens, Mark、Zhang, ChunHao、Crudden, Cathleen M.

  DOI：——

  日期：——