(R,R)-1,3-二-(4-溴苄基)-2-氯八氢-2-(2Z)-巴豆基-1H-1,3,2-苯并二氮杂硅杂环戊烷 | 804559-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R,R)-1,3-二-(4-溴苄基)-2-氯八氢-2-(2Z)-巴豆基-1H-1,3,2-苯并二氮杂硅杂环戊烷
• 英文名称: (R,R)-crotylsilane
• 英文别名: (3aR,7aR)-1,3-bis[(4-bromophenyl)methyl]-2-[(Z)-but-2-enyl]-2-chloro-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazasilole
• CAS: 804559-38-4
• 化学式: C₂₄H₂₉Br₂ClN₂Si
• 分子量: 568.854
• InChiKey: ZRWSDIWSVXXBNG-OPSVEJGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苄氧基乙醛 、 (R,R)-1,3-二-(4-溴苄基)-2-氯八氢-2-(2Z)-巴豆基-1H-1,3,2-苯并二氮杂硅杂环戊烷 以 二氯甲烷 为溶剂， 反应 20.0h， 以82%的产率得到(2R,3R)-1-benzyloxy-3-methyl-4-penten-2-ol
  参考文献：
  名称：

  A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation

  摘要：

  The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents - substrate scope - has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.

  DOI：

  10.1021/ja200712f
• 作为产物：
  描述：

  (Z)-crotyltrichlorosilane 、 (R,R)-N,N'-bis(4-bromobenzyl)cyclohexane-1,2-diamine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(R,R)-1,3-二-(4-溴苄基)-2-氯八氢-2-(2Z)-巴豆基-1H-1,3,2-苯并二氮杂硅杂环戊烷
  参考文献：
  名称：

  Highly Diastereo- and Enantioselective Reagents for Aldehyde Crotylation

  摘要：

  Two new, crystalline solid, storable, and highly enantioselective reagents for aldehyde crotylation have been developed. Both (cis and trans) crotylsilane reagents are easily prepared in bulk, require trivial reaction conditions, and provide the homoallylic alcohol products with near diastereo- and enantiospecificity in many cases.

  DOI：

  10.1021/ol0480731

文献信息

• Ir(I)-Catalyzed Enantioselective Decarboxylative Allylic Etherification: A General Method for the Asymmetric Synthesis of Aryl Allyl Ethers
  作者：Dongeun Kim、Srinivasa Reddy、Om V. Singh、Jae Seung Lee、Suk Bin Kong、Hyunsoo Han

  DOI：10.1021/ol3033237

  日期：2013.2.1

  Ir(I)-catalyzed enantioselective decarboxylative allylic etherification of aryl allyl carbonates provides aryl allyl ethers. Key to the generality and high stereoselection of the reaction is the use of the intramolecular decarboxylative allylation process and [Ir(dbcot)Cl]2 as an Ir(I) source. Ir(I)-catalyzed diastereoselective decarboxylative allylic etherification, combined with asymmetric aldehyde

  Ir（I）催化的芳基碳酸烯丙酯的对映选择性脱羧烯丙基醚化反应提供了芳基烯丙基醚。反应的一般性和高立体选择的关键是使用分子内脱羧烯丙基化过程和[Ir（dbcot）Cl] 2作为Ir（I）来源。Ir（I）催化的非对映选择性脱羧烯丙基醚化反应，与不对称醛的crotylation和交叉复分解相结合，可以提供具有高非对映选择性的单保护的2-甲基-1,3-二醇（从简单的醛开始）。
• COMPOSITIONS AND METHODS FOR STEREOSELECTIVE ALDEHYDE ALLYLATION AND CROTYLATION
  申请人：KIM Hyunwoo

  公开号：US20120190875A1

  公开（公告）日：2012-07-26

  Compositions and methods for practical, stereoselective allylation and crotylation for aldehyde substrates are described. The compositions and methods comprise reagents for allylation and/or crotylation and acids. In some embodiments, the reagents and acids are pre-mixed.

  本发明描述了一种用于醛底物的实用、立体选择性的烯丙基化和丙烯基化的组合物和方法。该组合物和方法包括用于烯丙基化和/或丙烯基化的试剂和酸。在一些实施例中，试剂和酸是预混合的。
• Enantioselective Allylation and Crotylation of in situ Generated β,γ-Unsaturated Aldehydes
  作者：Mark Lautens、J. McCubbin、Matthew Maddess

  DOI：10.1055/s-0031-1289565

  日期：2011.12

  β,γ-Unsaturated aldehydes generated in situ by treatment of 2-vinyloxiranes with a catalytic amount of Sc(OTf)3 are effectively trapped by ring-strained allyl- and crotylsilane reagents to afford bishomoallylic alcohols as single diastereomers in high enantiomeric excess.

  用催化量的 Sc(OTf)3 处理 2-乙烯基环氧乙烷原位生成的 β,γ-不饱和醛被环应变烯丙基和巴豆基硅烷试剂有效捕获，以高对映体过量的形式提供双烯丙基醇作为单一非对映体。
• The Enantioselective Allylation and Crotylation of Sterically Hindered and Functionalized Aryl Ketones: Convenient Access to Unusual Tertiary Carbinol Structures
  作者：Noah Z. Burns、Blaine M. Hackman、Pui Yee Ng、Ian A. Powelson、James L. Leighton

  DOI：10.1002/anie.200600910

  日期：2006.6.2
• A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation
  作者：Hyunwoo Kim、Stephen Ho、James L. Leighton

  DOI：10.1021/ja200712f

  日期：2011.5.4

  The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents - substrate scope - has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.