(E)-tert-butyl(6-iodohex-5-en-1-yloxy)diphenylsilane | 371172-65-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-tert-butyl(6-iodohex-5-en-1-yloxy)diphenylsilane
• 英文别名: 6-tert-butyldiphenylsilyloxy-1-iodo-1-hexene；tert-butyl-[(E)-6-iodohex-5-enoxy]-diphenylsilane
• CAS: 371172-65-5
• 化学式: C₂₂H₂₉IOSi
• 分子量: 464.462
• InChiKey: XOHXJDISOMCKDS-LDADJPATSA-N

物化性质

• 沸点：
  448.9±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl(6-iodohex-5-en-1-yloxy)diphenylsilane 在 Grubbs catalyst first generation lithium aluminium tetrahydride 、 正丁基锂 、 迭氮酸 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 Petroleum ether 、 苯 为溶剂， 反应 69.5h， 生成 (S)-2-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Cleavage of a chiral auxiliary using RCM on an especially sterically crowded alkene: Syntheses of chiral carbo- and heterocycles

  摘要：

  Chiral 1,5-, 1,6-, and 1,7-dienes generated in 3-4 steps from chiral auxiliary p-menthane-3-carboxaldehyde undergo RCM with notable discrepancies in reactivity depending on the nature and number of substituents flanking the central double bond. The chiral auxiliary is thus cleaved releasing a carbo- or heterocycle in the process. Special features concerning the RCM on these especially crowded systems are discussed. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.07.028
• 作为产物：
  描述：

  1-(tert-butyldiphenylsilyloxy)-5-hexyne 在 二氯二茂锆 、 二异丁基氢化铝 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以96%的产率得到(E)-tert-butyl(6-iodohex-5-en-1-yloxy)diphenylsilane
  参考文献：
  名称：

  Stereoselective Synthesis of Conjugated Trienols from Allylic Alcohols and 1-Iodo-1,3-dienes

  摘要：

  The stereoselective synthesis of conjugated trienes has been achieved from allylic alcohols and 1-iodo-1,3-dienes using Pd(OAc)(2)/AgOAc.

  DOI：

  10.1021/ol302719e

文献信息

• MONITORING AND ASSESSING DEACETYLASE ENZYME ACTIVITY
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160138077A1

  公开（公告）日：2016-05-19

  Disclosed herein are compounds and methods for detecting enzyme activity. In some embodiments, the enzyme is a deacetylase enzyme such as HDAC. The compound of the invention comprises a detectable label, a linker, and an enamide group. The compound can be enzymatically cleaved by the enzyme of interest to produce a nucleophilic fragment that includes the detectable label. Measurement of a signal generated by the detectable label can indicate enzyme activity. The compounds can be used as either in vivo or in vitro enzyme probes.

  本文披露了一种检测酶活性的化合物和方法。在某些实施例中，该酶是去乙酰化酶，如HDAC。该发明的化合物包括可检测的标记、连接剂和烯酰胺基团。该化合物可以被感兴趣的酶酶切割，产生包含可检测标记的亲核片段。通过测量可检测标记产生的信号可以指示酶活性。这些化合物可以用作体内或体外酶探针。
• Ag(I)-promoted Suzuki–Miyaura cross-couplings of n -alkylboronic acids
  作者：Gang Zou、Y.Krishna Reddy、J.R. Falck

  DOI：10.1016/s0040-4039(01)01536-2

  日期：2001.10

  Ag(I) salts significantly enhance palladium-catalyzed Suzuki-Miyaura cross-couplings of n-alkylboronic acids with a wide variety of aryl and alkenyl halides/triflates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Sterically Biased 3,3-Sigmatropic Rearrangement of Chiral Allylic Azides: Application to the Total Syntheses of Alkaloids
  作者：Sophie Lauzon、François Tremblay、David Gagnon、Cédrickx Godbout、Christine Chabot、Catherine Mercier-Shanks、Stéphane Perreault、Hélène DeSève、Claude Spino

  DOI：10.1021/jo800817p

  日期：2008.8.1

  We describe a tandem Mitsunobu/3,3-sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carboor heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.
• Suzuki–Miyaura cross-coupling of lithium n-alkylborates
  作者：Gang Zou、J.R Falck

  DOI：10.1016/s0040-4039(01)01128-5

  日期：2001.8

  The palladium-catalyzed cross-coupling of lithium n-alkylborates, generated in situ via addition of see-butyl lithium to boronate esters, proceeds in moderate to good yields with a wide variety of electrophiles. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective Synthesis of Conjugated Trienols from Allylic Alcohols and 1-Iodo-1,3-dienes
  作者：Damien Brandt、Véronique Bellosta、Janine Cossy

  DOI：10.1021/ol302719e

  日期：2012.11.2

  The stereoselective synthesis of conjugated trienes has been achieved from allylic alcohols and 1-iodo-1,3-dienes using Pd(OAc)(2)/AgOAc.