ethyl 6-bromohex-2-enoate | 71032-10-5

• 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: ethyl 6-bromohex-2-enoate
• 英文别名: Ethyl 6-bromhex-2-enoat；6-bromo-hex-2-enoic acid ethyl ester
• CAS: 71032-10-5
• 化学式: C₈H₁₃BrO₂
• 分子量: 221.094
• InChiKey: WOOMUBXIVURAHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 6-bromohex-2-enoate 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以87%的产率得到(E)-6-bromohex-2-en-1-ol
  参考文献：
  名称：

  4,5-Diisopropyl-B-[(E)-[(3‘-menthofuryl)dimethylsilyl]allyl]-1,3,2- dioxaborolane, an Improved Chiral Reagent for the Anti α-Hydroxyallylation of Aldehydes:  Application to the Enantioselective Synthesis of (−)-Swainsonine

  摘要：

  Diisopropyl tartrate-modified (E)-[gamma-(furyldimethylsilyl)allyl]boronates 10 and 11 were designed for the enantioselective synthesis of substituted anti-3,4-dihydroxy-1-butenes 9 via the anti-alpha-hydroxyallylation of aldehydes. The reactions of aldehydes with 10 and 11 provided furyldimethylsilyl-substituted anti-1,2-silanols 12 and 13 with good enantioselectivity (74-82% ee), and the silanols were oxidized to the corresponding anti-1,2-diols 9 by a modified Fleming-Tamao oxidation protocol. The high reactivity of the (menthofuryl)silane unit toward electrophilic substitution allowed complete protodesilylation of menthofuryl-substituted silanols 13 and subsequent oxidation to diols 9 in a one-pot operation without competing protodesilylation of the allylsilane unit. However, a two-step protocol was required for the protodesilylation-oxidation of the less reactive 2-(5-methyl)-asymmetric reactions with three chiral aldehydes 23-35 (80 to >92% de, with the exception of the mismatched reactions with aldehyde 25, which were essentially unselective). However, [[[2-(5-methylfuryl)]dimethylsilyl]ally]boronate 10 could only be synthesized in less than or equal to 15% yield, and oxidations of the 2-(5-methylfuryl)-substituted silanols 12 were lower-yielding than oxidations of the corresponding menthofuryl-substituted silanols 13. Thus diisopropyl tartrate-modified (E)-[gamma-[(menthofuryl)dimethylsilyl]ally]boronate 11 proved to be the more useful of the two reagents. As a demonstration of the utility of 11 in the synthesis of polyhydroxylated natural products, this new reagent was used in a brief and highly stereoselective synthesis of the naturally occurring alkaloid (-)-swainsonine (42).

  DOI：

  10.1021/jo961840s
• 作为产物：
  描述：

  4-溴丁醛 、 磷酰基乙酸三乙酯 生成 ethyl 6-bromohex-2-enoate
  参考文献：
  名称：

  Conformational effects on the 2,3-sigmatropic shift of sulfur-stabilized ylides and enolates involving bicyclic transition states

  摘要：

  DOI：

  10.1021/jo01332a029

文献信息

• Production method of capsinoid by dehydrating condensation, stabilizing method of capsinoid, and capsinoid composition
  申请人：Amino Yusuke

  公开号：US20070020738A1

  公开（公告）日：2007-01-25

  Capsinoids of formula (3) may be conveniently prepared in a high yield, in a short time, without using a dehydrating agent by esterification of a fatty acid of formula (1) with a hydroxymethylphenol of formula (2) using an enzyme without a solvent or in a low-polar solvent. Addition of a fatty acid represented by formula (4) is effective for stabilizing the ester compound of formula (3). wherein each symbol is as defined in the specification.

  公式（3）的辣椒素类化合物可以通过使用酶而不使用脱水剂，在无溶剂或低极性溶剂中，将公式（1）的脂肪酸与公式（2）的羟甲基酚酯化反应，高产率地、短时间内方便地制备。公式（4）表示的脂肪酸的加入对于稳定公式（3）的酯化合物是有效的。其中每个符号如规范中所定义。
• PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION, STABILIZING METHOD OF CAPSINOID, AND CAPSINOID COMPOSITION
  申请人：AMINO Yusuke

  公开号：US20100152291A1

  公开（公告）日：2010-06-17

  Capsinoids of formula (3) may be conveniently prepared in a high yield, in a short time, without using a dehydrating agent by esterification of a fatty acid of formula (1) with a hydroxymethylphenol of formula (2) using an enzyme without a solvent or in a low-polar solvent. Addition of a fatty acid represented by formula (4) is effective for stabilizing the ester compound of formula (3). wherein each symbol is as defined in the specification.

  公式（3）的辣椒素类物质可以通过使用酶而不使用脱水剂，在不使用溶剂或低极性溶剂的情况下，通过将公式（1）的脂肪酸与公式（2）的羟甲基酚酯化反应，高产率地、短时间内方便地制备。公式（4）代表的脂肪酸的添加对于稳定公式（3）的酯化物也是有效的。其中每个符号如规范中所定义。
• 5-Norbornene-2-carboxylic acid: Another catalytic mediator for Catellani-type reactions
  作者：Ze-Shui Liu、Guangyin Qian、Qianwen Gao、Peng Wang、Hong-Gang Cheng、Yu Hua、Qianghui Zhou

  DOI：10.1016/j.tet.2019.01.033

  日期：2019.3

  Mediators play a central role in Catellani-type reactions. Herein we reported the discovery of inexpensive 5-norbornene-2-carboxylic acid (N-4) as a general catalytic mediator (20 mol%) to facilitate ortho C-H activation and the following C-C bond formation of aryl iodides. Firstly, a cooperative catalytic system comprising N-4 and a palladium/XPhos complex was developed for the novel Catellani/redox-relay Heck cascade to construct tetrahydronaphthalenes and indanes that contain a quaternary carbon stereogenic center. The striking feature of this work was the avoidance of stoichiometric NBE mediator that are usually required for Catellani-type reactions. Then, preliminary results demonstrated that N-4 could act as a general catalytic mediator to replace NBE for other Catellani-type reactions, which will undoubtedly inspire future developments in the field of cooperative catalysis. Finally, control experiments indicated that the carboxylic acid moiety of N-4 plays an essential role in its ability to serve as a superior mediator. (C) 2019 Elsevier Ltd. All rights reserved.
• Conformational effects on the 2,3-sigmatropic shift of sulfur-stabilized ylides and enolates involving bicyclic transition states
  作者：Edwin Vedejs、Michael J. Arnost、James P. Hagen

  DOI：10.1021/jo01332a029

  日期：1979.8
• PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION AND STABILIZING METHOD OF CAPSINOID
  申请人：Ajinomoto Co., Inc.

  公开号：EP1853547B1

  公开（公告）日：2014-11-12