(E)-8-benzyloxycarbonylamino-3-octen-2-one | 154499-09-9

• 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: (E)-8-benzyloxycarbonylamino-3-octen-2-one
• 英文别名: (E)-benzyl 7-oxooct-5-enylcarbamate；benzyl N-[(E)-7-oxooct-5-enyl]carbamate
• CAS: 154499-09-9
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: VMVYTJDDYIEJGD-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-8-benzyloxycarbonylamino-3-octen-2-one 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 甲醇 为溶剂， 生成 (E)-benzyl 7-hydroxyoct-5-enylcarbamate
  参考文献：
  名称：

  Construction of Chiral 2-Functionalized PiperidineviaEnzymatic Resolution and Palladium-catalyzed N-Alkylation

  摘要：

  通过酶解外消旋醇 (1) 得到的光学活性脲[(-)-1]在钯催化下发生环化反应，生成了哌啶 6。该反应实现了高效的分子内手性转移。化合物 6 被转化为 (+)- 科尼因和 2- 羟甲基哌啶。

  DOI：

  10.1246/cl.1994.21
• 作为产物：
  描述：

  5-(Z-氨基)-1-戊醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (E)-8-benzyloxycarbonylamino-3-octen-2-one
  参考文献：
  名称：

  Construction of Chiral 2-Functionalized PiperidineviaEnzymatic Resolution and Palladium-catalyzed N-Alkylation

  摘要：

  通过酶解外消旋醇 (1) 得到的光学活性脲[(-)-1]在钯催化下发生环化反应，生成了哌啶 6。该反应实现了高效的分子内手性转移。化合物 6 被转化为 (+)- 科尼因和 2- 羟甲基哌啶。

  DOI：

  10.1246/cl.1994.21

文献信息

• Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines
  作者：Xian-Dong Zhai、Zhong-Duo Yang、Zhi Luo、Hong-Tao Xu

  DOI：10.1016/j.cclet.2017.04.017

  日期：2017.8

  Abstract An intramolecular organocatalytic enantioselective aza-Michael reaction of carbamates, sulfonamides and acetamides to α,β-unsaturated ketones was developed. This process is promoted by 9-amino-9-deoxy-epi-quinine and diphenyl hydrogen phosphate to afford a straightforward and expeditious synthesis of several synthetically useful five- and six-membered heterocycles with excellent enantioselectivity

  摘要建立了氨基甲酸酯，磺酰胺和乙酰胺对α，β-不饱和酮的分子内有机催化对映选择性氮杂-迈克尔反应。9-氨基-9-脱氧-表奎宁和磷酸二苯酯促进了该过程，从而快速，快速地合成了几种合成有用的五元和六元杂环，具有出色的对映选择性（92％–97.5％ee），并且良率极高（高达99％）。
• Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones
  作者：Santos Fustero、Carlos del Pozo、Cristina Mulet、Rubén Lazaro、María Sánchez-Roselló

  DOI：10.1002/chem.201101292

  日期：2011.12.9

  AbstractAn organocatalytic enantioselective intramolecular aza‐Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9‐amino‐9‐deoxy‐epi‐hydroquinine as the catalyst and pentafluoropropionic acid as a co‐catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo‐fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.
• Synthesis and Antimalarial Activity of dl-Deoxyfebrifugine
  作者：Yasuo Takeuchi、Shin-ichiro Tokuda、Tomoko Takagi、Midori Koike、Hitoshi Abe、Takashi Harayama、Yasuharu Shibata、Hye-sook Kim、Yusuke Wataya

  DOI：10.3987/com-99-8564

  日期：——

  dl-Deoxyfebrifugine (3) was synthesized from 2-piperidone (4) by two methods via the Wittig reaction of 2-hydroxypiperidine (6). The antimalarial activity of 3 was discussed.
• Construction of Chiral 2-Functionalized Piperidine<i>via</i>Enzymatic Resolution and Palladium-catalyzed N-Alkylation
  作者：Yoshiro Hirai、Mayumi Nagatsu

  DOI：10.1246/cl.1994.21

  日期：1994.1

  The palladium-catalyzed cyclization of the optically active urethan [(−)-1], which was obtained by enzymatic resolution of the racemic alcohol (1), gave the piperidine 6. This reaction affords highly efficient intramolecular chirality transfer. Compound 6 was converted into (+)-coniine and 2-hydroxymethylpiperidine.

  通过酶解外消旋醇 (1) 得到的光学活性脲[(-)-1]在钯催化下发生环化反应，生成了哌啶 6。该反应实现了高效的分子内手性转移。化合物 6 被转化为 (+)- 科尼因和 2- 羟甲基哌啶。