(2-bromoethylidene)cyclopentane | 931-42-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (2-bromoethylidene)cyclopentane
• 英文别名: 2-bromoethylidenecyclopentane
• CAS: 931-42-0
• 化学式: C₇H₁₁Br
• 分子量: 175.068
• InChiKey: BQOYKRPKRYFJSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2-bromoethylidene)cyclopentane 在 氢氧化钾 、 2-硝基丙烷 、 叔丁醇 作用下， 生成 cyclopentylidenacetaldehyde
  参考文献：
  名称：

  Marcou,A.; Normant,H., Bulletin de la Societe Chimique de France, 1966, p. 1400 - 1404

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(cyclopentylidene)ethanol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (2-bromoethylidene)cyclopentane
  参考文献：
  名称：

  手性 1,2,3-三唑盐催化 2,5-二酮哌嗪的不对称单烷基化和二烷基化以及四取代碳中心的构建

  摘要：

  手性螺环酰胺衍生的三唑鎓盐被用作不对称烷基化的新型相转移有机催化剂，以高产率构建含有一个或两个四取代碳中心的 2,5-二酮哌嗪基序，具有优异的顺式-非对映选择性和对映选择性。对照实验和 DFT 计算揭示了可能的反应机理和异常非对映选择性和对映选择性的起源。

  DOI：

  10.1002/anie.202114129

文献信息

• Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing <i>N</i>-Heterocycles via Dual Cobaloxime and Photoredox Catalysis
  作者：Jia-Lin Tu、Jia-Li Liu、Wan Tang、Ma Su、Feng Liu

  DOI：10.1021/acs.orglett.0c00224

  日期：2020.2.7

  Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole

  天然和合成生物活性分子中都普遍存在含氮杂环。我们在本文中报道了一种空前的协议，用于通过协同光氧化还原和钴肟催化的α-亚氨基-氧酸与侧链烯烃的氮杂氮环化。在有或没有烯烃作为分子间交叉偶联伴侣的情况下，转化以令人满意的产率提供了多种相应的含烯烃的二氢吡咯产物。在存在外部烯烃的情况下，串联反应产生具有优异的化学和立体选择性的E-选择性偶联产物。
• Cu-Catalyzed Aminoacyloxylation of Unactivated Alkenes of Unsaturated Hydrazones with Manifold Carboxylic Acids toward Ester-Functionalized Pyrazolines
  作者：Rui-Hua Liu、Zi-Qing Wang、Bang-Yi Wei、Jian-Wu Zhang、Bo Zhou、Bing Han

  DOI：10.1021/acs.orglett.8b01507

  日期：2018.7.20

  A copper-catalyzed aminoacyloxylation of unactivated alkenes of unsaturated hydrazones is achieved by using various commercially available carboxylic acids as the acyloxylating reagents and di-tert-butyl peroxide (DTBP) as the oxidant. By using this method, a sequence of structurally diversiform acyloxyl-substituted pyrazolines are efficiently synthesized. Significantly, many carboxyl-containing drugs

  不饱和的未活化烯烃的铜催化氨基酰氧基化反应是通过使用各种可商购的羧酸作为酰氧基化试剂，并使用二叔丁基过氧化物（DTBP）作为氧化剂来实现的。通过使用这种方法，可以有效地合成一系列结构多样的酰氧基取代的吡唑啉。重要的是，许多含羧基的药物和具有未保护官能团的生物活性分子在该反应中是相容的。
• Synthesis of Functionalized Furans via Gold(I)-Catalyzed Claisen-Type Rearrangement
  作者：Florin M. Istrate、Fabien L. Gagosz

  DOI：10.1021/jo7022685

  日期：2008.1.1

  Gold(I)-catalyzed cyclization of pentenynyl allyl ethers allows the rapid construction of functionalized furans. The concerted oxy-Claisen-type mechanism induces a complete selectivity of the process and allows the easy formation of quaternary centers.

  金（I）催化的戊炔基烯丙基醚的环化可快速构建官能化的呋喃。一致的氧-克莱森型机理诱导了该过程的完全选择性，并易于形成四元中心。
• Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers
  作者：Florin M Istrate、Fabien Gagosz

  DOI：10.3762/bjoc.7.100

  日期：——

  A series of ynenyl allyl ethers were rearranged into polysubstituted furans in the presence of a gold(I) catalyst. It is proposed that the transformation involves a Claisen-type rearrangement that allows the efficient creation of quaternary centers under mild experimental conditions.

  在金（I）催化剂的存在下，一系列炔基烯丙基醚被重排成多取代呋喃。建议转换涉及克莱森型重排，允许在温和的实验条件下有效创建四元中心。
• Cyclopropanecarboxylic acids and esters
  申请人：Roussel-UCLAF

  公开号：US03997586A1

  公开（公告）日：1976-12-14

  Novel cyclopropanecarboxylic acids and esters of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are selected from the group consisting of hydrogen, alkyl, aralkyl, aryl, alkenyl non-conjugated with the cyclopropane ring, alkenyl non-conjugated with the cyclopropane ring, cycloalkyl, cycloalkenyl and heterocyclic; R is selected from the group consisting of OH and OR' in which R' is selected from the group consisting of lower alkyl which may be substituted, benzyl which may be substituted on the phenyl or methylene portion, N-methylene-dicarboximide, (5-benzyl-furyl-3) methyl, and a cyclopentene of the formula ##STR2## WHEREIN R" is selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic; A is a bivalent alkyl radical selected from the group consisting of ##STR3## WHEREIN R.sub.1 is selected from the group consisting of hydrogen and lower alkyl, R.sub.2 and R.sub.3 are selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic and taken together with the carbon atom to which they are attached form a ring selected from the group consisting of carbon homo rings and unsaturated carbon homo rings of 3 to 7 carbon atoms and heterocyclic rings which may be substituted with lower alkyl or lower alkoxy and R.sub.2 and R.sub.3 may together form a polycyclic aromatic radical, R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached may form a saturated or unsaturated carbon homo ring or a heterocyclic ring, Y is selected from the group consisting of methylene and a saturated or unsaturated carbon chain and Y' is selected from the group consisting of methine and a saturated or unsaturated carbon chain with the proviso that when Z.sub.1 and Z.sub.2 are methyl and R.sub.1 is hydrogen, R.sub.2 is other than methyl and their preparation.

  新型环丙烷羧酸及其酯类化合物，其通式为##STR1##其中Z1和Z2选自氢、烷基、芳烷基、芳基、非共轭于环丙烷环的烯基、非共轭于环丙烷环的烯基、环烷基、环烯基和杂环；R选自OH和OR'，其中R'选自可能被取代的低级烷基、可能被取代在苯基或亚甲基部分的苄基、N-亚甲基二羧亚胺、(5-苄基-呋喃-3)甲基，以及通式为##STR2##的环戊烯，其中R"选自烷基、炔基、烯基、芳基、芳烷基、环烷基、环烯基和杂环；A为选自以下结构的二价烷基基团：##STR3##其中R1选自氢和低级烷基，R2和R3选自烷基、炔基、烯基、芳基、芳烷基、环烷基、环烯基和杂环，并与它们所连接的碳原子一起形成选自3至7个碳原子的碳同环和非饱和碳同环以及可能被低级烷基或低级烷氧基取代的杂环环，R2和R3可以一起形成多环芳香族基团，R4为低级烷基，R5选自氢和低级烷基，且R4和R5与它们所连接的碳原子一起可以形成饱和或非饱和碳同环或杂环环，Y选自亚甲基和饱和或非饱和碳链，Y'选自甲川基和饱和或非饱和碳链，但当Z1和Z2为甲基且R1为氢时，R2不得为甲基，以及它们的制备方法。