(E)-[1-{6-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hex-3-enylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester | 847550-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-[1-{6-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hex-3-enylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: (E)-di-tert-butyl ((2S,2'S)-(hex-3-ene-1,6-diylbis(azanediyl))bis(3-(1H-indol-3-yl)-1-oxopropane-1,2-diyl))dicarbamate；di-tert-butyl ((2S,2'S)-(hex-3-ene-1,6-diylbis(azanediyl))bis(3-(1H-indol-3-yl)-1-oxopropane-1,2-diyl))dicarbamate；tert-butyl N-[(2S)-3-(1H-indol-3-yl)-1-[[(E)-6-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]hex-3-enyl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 847550-13-4
• 化学式: C₃₈H₅₀N₆O₆
• 分子量: 686.852
• InChiKey: XJNRDBLXFDKSQX-UMPLPVRUSA-N

物化性质

• 沸点：
  968.0±65.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-[1-{6-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hex-3-enylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-[1-{6-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hex-3-enylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Self-Selection in Olefin Cross-Metathesis:  The Effect of Remote Functionality

  摘要：

  [GRAPHICS]Olefin cross-metathesis (CM) is potentially an attractive method for generating dynamic combinatorial libraries (DCLs). In order for the CM reaction to be useful for DCL production, the course of the reaction and product distribution must be relatively insensitive to functionality remote from the reacting centers. We report on the CM of a series of allyl- and homoallylamides that are strongly dependent on remote functionality. This includes an unusual example of a cis-selective CM.

  DOI：

  10.1021/ol047361u
• 作为产物：
  描述：

  (Z)-[1-{6-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hex-3-enylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-[1-{6-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hex-3-enylcarbamoyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Self-Selection in Olefin Cross-Metathesis:  The Effect of Remote Functionality

  摘要：

  [GRAPHICS]Olefin cross-metathesis (CM) is potentially an attractive method for generating dynamic combinatorial libraries (DCLs). In order for the CM reaction to be useful for DCL production, the course of the reaction and product distribution must be relatively insensitive to functionality remote from the reacting centers. We report on the CM of a series of allyl- and homoallylamides that are strongly dependent on remote functionality. This includes an unusual example of a cis-selective CM.

  DOI：

  10.1021/ol047361u

文献信息

• Z-Selective Olefin Metathesis on Peptides: Investigation of Side-Chain Influence, Preorganization, and Guidelines in Substrate Selection
  作者：Shane L. Mangold、Daniel J. O’Leary、Robert H. Grubbs

  DOI：10.1021/ja507166g

  日期：2014.9.3

  modulating the stability and activity of biologically relevant compounds; however, the ability to control olefin geometry in the product remains a challenge. Recent advances in the design of cyclometalated ruthenium catalysts has led to new strategies for achieving such control with high fidelity and Z selectivity, but the scope and limitations of these catalysts on substrates bearing multiple functionalities

  烯烃复分解已成为调节生物相关化合物的稳定性和活性的有前途的策略；然而，控制产品中烯烃几何形状的能力仍然是一个挑战。环金属化钌催化剂设计的最新进展催生了实现这种高保真度和Z选择性控制的新策略，但这些催化剂在具有多种功能（包括肽）的基质上的范围和局限性仍有待探索。在此，我们报告了对肽的生产性和非生产性 Z 选择性复分解的各种因素的评估。通过同二聚化、交叉复分解和闭环复分解探索了空间、侧链同一性和通过肽二级结构的预组织的影响。我们的结果表明，氨基酸侧链和烯烃的特性深刻影响环金属化钌催化剂在Z-选择性复分解中的活性。不同肽底物上的交叉复分解和闭环复分解强调了实现高转化率和 Z 选择性的标准。本报告中概述的原理不仅对于扩大 Z-选择性烯烃复分解到肽的范围很重要，而且对于在一般合成工作中应用立体选择性烯烃复分解也很重要。