1-Brom-4-phenyl-but-2-in | 3182-70-5

• 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: 1-Brom-4-phenyl-but-2-in
• 英文别名: 1-Bromo-4-phenyl-2-butyne；4-bromobut-2-ynylbenzene
• CAS: 3182-70-5
• 化学式: C₁₀H₉Br
• 分子量: 209.085
• InChiKey: WEDWLVGEBOGHGO-UHFFFAOYSA-N

物化性质

• 沸点：
  142-143 °C(Press: 12 Torr)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-Brom-4-phenyl-but-2-in 在 Novozym 435 、 sodium iodide 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 95.0h， 生成 (R)-(+)-4-(benzyl)hexa-1,4,5-trien-1-yn-3-yl acetate
  参考文献：
  名称：

  Novozym-435-catalyzed efficient preparation of (1S)-ethenyl and ethynyl 2,3-allenols and (1R)-ethenyl and ethynyl 2,3-allenyl acetates with high enantiomeric excess

  摘要：

  Novozym-435 (a form of Candida antarctica lipase B) was found to be an effective biocatalyst for the kinetic resolution of a variety of racemic I-ethenyl or ethynyl-substituted 2,3-allenols. The optically active 1-ethynyl-substituted 2,3-allenols can be subjected to Sonogashira coupling reactions and alkylations of terminal C-C triple bonds leading to the formation of 2,3-allenols, which cannot be directly prepared by Novozym 435-catalyzed kinetic resolution probably due to the steric hindrance. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.048
• 作为产物：
  描述：

  4-phenyl-2-butyn-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以53%的产率得到1-Brom-4-phenyl-but-2-in
  参考文献：
  名称：

  苯并咪唑啉通过光诱导的电子转移，通过苯甲酰基化合物形成碳-碳键

  摘要：

  发现在烯丙基溴的存在下，苯甲酰基化合物如苯甲酰基甲酸酯衍生物与2-（对茴香基）-1，3-二甲基苯并咪唑啉之间的光反应产生了各种烯丙基化的醇。在苯甲酰基甲酸酯的反应中，建议通过苯并咪唑啉向光激发的苯甲酰基甲酸酯的电子转移，作为中间体生成α-羟基酯烯酸酯，其在苯甲酰基的羰基碳上带有负电荷。这些物质与烯丙基溴反应生成α-烯丙基-α-羟基酯。

  DOI：

  10.1016/j.tetlet.2013.10.028

文献信息

• Enantioselective Multicomponent Synthesis of Fused 6-5 Bicyclic 2-Butenolides by a Cascade Heterobicyclisation Process
  作者：Marcos G. Suero、Raquel De la Campa、Laura Torre-Fernández、Santiago García-Granda、Josefa Flórez

  DOI：10.1002/chem.201102288

  日期：2012.6.4

  heterobicyclisation products is the result of the regioselective integration of the Grignard reagent as a propargyl fragment followed by a cascade CO/alkyne/CO insertion, ketene trapping and elimination sequence. By using lithium enolates of chiral N‐acetyl‐2‐oxazolidinones and the corresponding propargylic organocerium reagents, both enantiomers of these bicyclic heterocycles were efficiently prepared with

  铬的烷氧基（芳基/杂芳基）卡宾络合物与酮或酰亚胺烯醇锂的连续偶联，然后与3-取代的（H，TMS，PhCH 2，PhCH 2 CH 2，Me）炔丙基有机镁试剂偶联具有三个模块化点的新型羟基取代双环[4.3.0]-γ-亚烷基-2-丁烯内酯，可有效引入分子复杂性，包括均丙醇核心。这些五或六组分异双环化产物的选择性形成是格氏试剂作为炔丙基片段进行区域选择性整合，随后是级联的CO /炔烃/ CO插入，乙烯酮捕获和消除序列的结果。通过使用手性N的烯醇锂对乙酰基-2-恶唑烷酮和相应的炔丙基有机铈试剂，均以非常高的对映体纯度有效地制备了这些双环杂环的对映体。在结构上，这些稠合的双环丁烯内酯的特征是高度不饱和和氧化的核，并且它们在溶液中显示出很强的蓝色荧光。
• 3-Benzyl-7-amino-3-cephem-4-carboxylic acid, the tertiary butyl ester,
  申请人：Beecham Group Limited

  公开号：US03974154A1

  公开（公告）日：1976-08-10

  3-BENZYL-7-AMINO-3-CEPHEM-4-CARBOXYLIC ACID AND ESTERS AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF.

  3-苄基-7-氨基-3-头孢-4-羧酸及其酯和药用可接受盐。
• The Renaissance of an Old Problem: Highly Regioselective Carboxylation of 2-Alkynyl Bromides with Carbon Dioxide
  作者：Bukeyan Miao、Gen Li、Shengming Ma

  DOI：10.1002/chem.201503494

  日期：2015.11.23

  A steric effect‐controlled, zinc‐mediated carboxylation of different 2‐alkynyl bromides under an atmospheric pressure of CO2 has been developed by careful tuning of different reaction parameters, including the metal, solvent, temperature, and additive. 2‐Substituted 2,3‐allenoic acids were afforded from primary 2‐alkynyl bromides, whereas the carboxylation of secondary 2‐alkynyl bromides yielded 3‐alkynoic

  通过仔细调节不同的反应参数（包括金属，溶剂，温度和添加剂），已开发出在CO 2大气压下，空间效应控制的锌介导的不同2-炔基溴化物的羧化反应。伯2-炔基溴化物可提供2-取代的2,3-烯丙酸，而仲2-炔基溴化物的羧化则可得到3-链炔酸，且得率较高。已经提出了观察到的区域选择性的基本原理。
• Cyclohexenone oxime ethers, their preparation, intermediates for their
  申请人：BASF Aktiengesellschaft

  公开号：US05250505A1

  公开（公告）日：1993-10-05

  Cyclohexenone oxime ethers I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is unsubstituted or substituted C.sub.3 -C.sub.6 -alkynylene, Z is unsubstituted or substituted phenyl an unsubstituted or substituted 6-membered or 7-membered saturated or monounsaturated or diunsaturated heterocyclic structure having one or two hetero atoms selected from the group consisting of oxygen and sulfer, and their agriculturally useful salts and esters of C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids, are suitable as herbicides.

  环己烯酮肟醚I ##STR1## 其中R.sup.1是C.sub.1-C.sub.6-烷基，A是未取代或取代的C.sub.3-C.sub.6-炔基，Z是未取代或取代的苯基，未取代或取代的有一或两个氧和硫的杂原子的6-或7-成员饱和或单不饱和或二不饱和杂环结构，其农业上有用的C.sub.1-C.sub.10-羧酸盐和无机酸酯，适用于除草剂。
• Cyclohexenone oxime ethers and their use as herbicides
  申请人：BASF Aktiengesellschaft

  公开号：US05374609A1

  公开（公告）日：1994-12-20

  Cyclohexenone oxime ethers I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is unsubstituted or substituted C.sub.3 -C.sub.6 -alkynylene, Z is unsubstituted or substituted phenyl or a 5-membered or 6-membered heteroaromatic and R.sup.2 is C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, unsubstituted or substituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.7 -cycloalkenyl, an unsubstituted or substituted 5-membered saturated heterocyclic structure having one or two hetero atoms, an unsubstituted or substituted 6-membered or 7-membered saturated or monounsaturated or diunsaturated heterocyclic structure having one or two hetero atoms, an unsubstituted or substituted 5-membered heteroaromatic having one to three hetero atoms or unsubstituted or substituted phenyl or pyridyl, and their agriculturally useful salts and esters of C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids, are suitable as herbicides.

  环己烯酮肟醚I，其中R1是C1-C6烷基，A是未取代或取代的C3-C6炔基亚基，Z是未取代或取代的苯基或5元或6元杂芳基，R2是C1-C4烷氧基-C1-C6烷基，C1-C4烷硫基-C1-C6烷基，未取代或取代的C3-C7环烷基或C5-C7环烯基，未取代或取代的含有一个或两个杂原子的5元饱和杂环结构，未取代或取代的含有一个或两个杂原子的6元或7元饱和或单不饱和或双不饱和杂环结构，未取代或取代的含有一到三个杂原子的5元杂芳基或未取代或取代的苯基或吡啶基，以及它们的C1-C10羧酸和无机酸的农业上有用的盐和酯，可用作除草剂。