3-benzyloxyhex-5-ene | 123401-91-2

• 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: 3-benzyloxyhex-5-ene
• 英文别名: 4-benzyloxyhexene；Hex-5-en-3-yloxymethylbenzene；hex-5-en-3-yloxymethylbenzene
• CAS: 123401-91-2
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: MJNZHRUSDDTSCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-benzyloxyhex-5-ene 在 Hoveyda-Grubbs catalyst second generation 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-5-phenylmethoxyhept-2-en-1-ol
  参考文献：
  名称：

  Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis

  摘要：

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.080
• 作为产物：
  描述：

  5-己烯-3-醇 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-benzyloxyhex-5-ene
  参考文献：
  名称：

  Yadav, J S; Rao, E Sreenivasa, Synthetic Communications, 1988, vol. 18, # 18, p. 2315 - 2324

  摘要：

  DOI：

文献信息

• A Modular Synthesis of Some Biologically Relevant Cyclic Peptides through Late-Stage Functionalization
  作者：Shital Chattopadhyay、Jyoti Mukherjee、Suman Sil、Amit Pahari

  DOI：10.1055/s-0035-1561561

  日期：——

  chain through cross metathesis. It is observed that while the cross-metathesis reaction of a terminal olefin having a β-substituent is marginally successful with the scaffold, the corresponding reaction with an α,β-unsaturated ketone/ester is more promising. The utility of the protocol is demonstrated through the preparation of three cyclic tetrapeptides structurally related to the novel histone deacetylase

  摘要 据报道一些与一类组蛋白脱乙酰基酶抑制剂有关的环肽的模块化合成。该合成利用环状四肽支架的后期功能化来通过交叉复分解连接烷基侧链。观察到，虽然具有β-取代基的末端烯烃的交叉复分解反应在支架上略微成功，但与α，β-不饱和酮/酯的相应反应更有希望。通过制备与新型组蛋白脱乙酰基酶抑制剂FR-225497和trapoxin B结构相关的三种环状四肽，证明了该方案的实用性。 据报道一些与一类组蛋白脱乙酰基酶抑制剂有关的环肽的模块化合成。该合成利用环状四肽支架的后期功能化来通过交叉复分解连接烷基侧链。观察到，虽然具有β-取代基的末端烯烃的交叉复分解反应在支架上略微成功，但与α，β-不饱和酮/酯的相应反应更有希望。通过制备与新型组蛋白脱乙酰基酶抑制剂FR-225497和trapoxin B结构相关的三种环状四肽，证明了该方案的实用性。
• Yadav, J S; Rao, E Sreenivasa, Synthetic Communications, 1988, vol. 18, # 18, p. 2315 - 2324
  作者：Yadav, J S、Rao, E Sreenivasa

  DOI：——

  日期：——
• Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.tet.2011.01.080

  日期：2011.3

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of the unusual α-amino acid component of some novel histone deacetylase inhibiting cyclic peptides
  作者：Amit K. Pahari、Jyoti Prasad Mukherjee、Shital K. Chattopadhyay

  DOI：10.1016/j.tet.2014.07.045

  日期：2014.10

  A flexible protocol for the synthesis of three lipophilic alpha-amino acid components of some novel cyclic peptides having important histone deacetylase inhibiting properties has been developed from a common source, which featured a cross-metathesis reaction between two unhindered terminal olefins as the key step. (C) 2014 Elsevier Ltd. All rights reserved.