tert-butyl 7-hydroxyhept-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl 7-hydroxyhept-2-enoate
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: KEFVQUXILJDCOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 7-hydroxyhept-2-enoate 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium methylate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 cesium fluoride 、 hexadecyltrimethylammonium bromide 、 三氟乙酸 、 三氟乙酸酐 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 正己烷 、 氯仿 、 二甲基亚砜 、 甲苯 为溶剂， 反应 145.25h， 生成 β-Lycorane
  参考文献：
  名称：

  Total Synthesis of (±)-α- and β-Lycoranes by Sequential Chemoselective Conjugate Addition−Stereoselective Nitro-Michael Cyclization of an ω-Nitro-α,β,ψ,ω-unsaturated Ester

  摘要：

  [GRAPHIC]An omega-nitro-alpha,beta,psi,omega-unsaturated ester underwent a chemoselective conjugate addition of a nitroolefin moiety with aryllithium to produce a psi-aryl-omega-nitro-alpha,beta-unsaturated ester, which was then stereoselectively cyclized by intramolecular nitro-Michael reaction giving a functionalized cyclohexane applicable to the total synthesis of (+/-)-alpha- and beta-lycoranes.

  DOI：

  10.1021/ol0341905

文献信息

• De-novo designed β-lysine derivatives can both augment and diminish the proliferation rates of E. coli through the action of Elongation Factor P
  作者：Ciara M. McDonnell、Magda Ghanim、J. Mike Southern、Vincent P. Kelly、Stephen J. Connon

  DOI：10.1016/j.bmcl.2022.128545

  日期：2022.3

  An investigation into the effect of modified β-lysines on the growth rates of eubacterial cells is reported. It is shown that the effects observed are due to the post translational modification of Elongation Factor P (EFP) with these compounds catalysed by PoxA. PoxA was found to be remarkably promiscuous, which allowed the activity of a wide range of exogenous β-lysines to be examined. Two chain-elongated

  报道了一项研究修饰的β-赖氨酸对真细菌细胞生长速率的影响。结果表明，观察到的效果是由于用 PoxA 催化的这些化合物对延伸因子 P (EFP) 进行了翻译后修饰。PoxA 被发现是非常混杂的，这使得可以检查广泛的外源 β-赖氨酸的活性。两种在氨基烷基链长度上仅相差 2 个碳单位的链延长的 β-赖氨酸衍生物表现出相反的生物活性——一种促进生长，另一种延缓生长。两种化合物均显示通过 EFP 的修饰起作用。
• Synthesis of Nitrogen-Functionalized Cyclohexanes Using Chemoselective Conjugate Addition of Phenyllithium to Linear .OMEGA.-Nitro-.ALPHA.,.BETA.,.PSI.,.OMEGA.-Unsaturated Ester and Subsequent Stereoselective Intramolecular Nitro-Michael Cyclization
  作者：Tomohisa Yasuhara、Katsumi Nishimura、Emi Osafune、Osamu Muraoka、Kiyoshi Tomioka

  DOI：10.1248/cpb.52.1109

  日期：——

  Nitrogen-functionalized cyclohexane derivatives with three contiguous chiral centers were synthesized by nitroalkene-selective conjugate addition of phenyllithium to a omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereocontrolled intramolecular nitro-Michael cyclization with cesium fluoride and a quaternary ammonium bromide. The cyclohexanes were applicable to the total synthesis

  氮官能化的具有三个连续手性中心的环己烷衍生物的合成方法是：将苯基锂与硝基烯烃选择性共轭加成至ω-硝基-α，β，psi，ω-不饱和酯中，然后通过氟化铯和季铵盐进行立体控制的分子内硝基-Michael环化反应溴化铵。环己烷适用于α-，β-和γ-环烷的全合成。
• A practical synthesis of protected β-homolysine
  作者：Markus Baenziger、Luca Gobbi、Bernard P Riss、Frank Schaefer、Andrea Vaupel

  DOI：10.1016/s0957-4166(00)00173-7

  日期：2000.6

  Protected beta-homolysine of high enantiomeric purity (ee > 99.5%) is prepared utilizing the stereoselective conjugate addition of lithiated (S)-(alpha-methylbenzyl)benzylamide to (E)-7-(tosyloxy)hept-2-enoic acid tert-butyl ester, followed by subsequent ammonia substitution, Boc protection and removal of the auxiliary. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of (±)-α- and β-Lycoranes by Sequential Chemoselective Conjugate Addition−Stereoselective Nitro-Michael Cyclization of an ω-Nitro-α,β,ψ,ω-unsaturated Ester
  作者：Tomohisa Yasuhara、Katsumi Nishimura、Mitsuaki Yamashita、Naoshi Fukuyama、Ken-ichi Yamada、Osamu Muraoka、Kiyoshi Tomioka

  DOI：10.1021/ol0341905

  日期：2003.4.1

  [GRAPHIC]An omega-nitro-alpha,beta,psi,omega-unsaturated ester underwent a chemoselective conjugate addition of a nitroolefin moiety with aryllithium to produce a psi-aryl-omega-nitro-alpha,beta-unsaturated ester, which was then stereoselectively cyclized by intramolecular nitro-Michael reaction giving a functionalized cyclohexane applicable to the total synthesis of (+/-)-alpha- and beta-lycoranes.