(E)-1-benzenesulfonyl-2-methyl-4-bromo-2-butene | 41856-34-2

• 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)-1-benzenesulfonyl-2-methyl-4-bromo-2-butene
• 英文别名: 1-(phenylsulfonyl)-3-methyl-4-bromo-2-butene；[[(2E)-4-Bromo-3-methyl-2-butenyl]sulfonyl]benzene；[(E)-4-bromo-3-methylbut-2-enyl]sulfonylbenzene
• CAS: 41856-34-2
• 化学式: C₁₁H₁₃BrO₂S
• 分子量: 289.193
• InChiKey: UUIYJJPMQNXCGE-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-benzenesulfonyl-2-methyl-4-bromo-2-butene 、 苯甲醛 在 indium 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-benzenesulfonyl-2-isopropenyl-1-phenylpropanol 、 3-benzenesulfonyl-2-isopropenyl-1-phenylpropanol
  参考文献：
  名称：

  Origin of the Diastereoselection in the Indium-Mediated Addition of Haloallylic Sulfones to Aldehydes

  摘要：

  The R-1 substituents at C(2) of the haloallylic sulfones 1 play a pivotal role in controlling the diastereoselectivity of the indium-mediated addition reaction to benzalclehyde to produce the homoallylic alcohols 3. The R, Me group of 1 prefers the chair form in the In-coordinated six-membered cyclic transition state to give anti-3a, and the R-1 Ph group of 1 favors the twist boat form to give syn-3n, both in a high 13:1 selectivity.

  DOI：

  10.1021/ol060297r
• 作为产物：
  描述：

  2-甲基-3-丁烯-2-醇 在 正丁基锂 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 (E)-1-benzenesulfonyl-2-methyl-4-bromo-2-butene
  参考文献：
  名称：

  γ-Lactone Formation in the Addition of Benzenesulfonyl Bromide to Diene and Enyne Esters

  摘要：

  The gem-dialkyl effect has been used to promote the formation of functionalized gamma-lactones in the addition of benzenesulfonyl bromide to diene and enyne esters. Introduction of 3 mol % of pyridine into the reactions increases the yields of lactones produced from tertiary esters. Formation of the C-alpha-C-beta bond of gamma-lactones has been achieved in both C-alpha-->C beta and C-beta-->C-alpha radical cyclization directions.

  DOI：

  10.1021/jo982388a

文献信息

• Process for producing allyl halide compound
  申请人：——

  公开号：US20020107422A1

  公开（公告）日：2002-08-08

  There are disclosed a composition comprising (E)-1,4-dibromo-2-methyl-2-butene and (Z)-1,4-dibromo-2-methyl-2-butene, wherein the ratio of the E isomer to the total amount of the E and Z isomers is 0.9 or more; a process for producing the same and a process using the same to produce an allyl halide compound of formula (1): 1 wherein X denotes a bromine atom, Y denotes an ArS(O) 2 group or an RCOO group, wherein Ar denotes an aryl group which may be substituted and R denotes a hydrogen atom, a lower alkyl group or an aryl group which may be substituted, and the wavy line means that the derivative is a mixture of an E or Z geometrical isomer.

  本发明涉及一种包含(E)-1,4-二溴-2-甲基-2-丁烯和(Z)-1,4-二溴-2-甲基-2-丁烯的组合物，其中E异构体与E和Z异构体的总量之比为0.9或更高；一种生产该组合物的方法以及使用该组合物生产化合物的方法，所述化合物的分子式为（1）：其中X代表溴原子，Y代表ArS(O)2基团或RCOO基团，其中Ar代表可能被取代的芳基，R代表氢原子、低碳烷基或可能被取代的芳基，波浪线表示衍生物是E或Z几何异构体的混合物。
• γ-Lactone Formation in the Addition of Benzenesulfonyl Bromide to Diene and Enyne Esters
  作者：Chen Wang、Glen A. Russell

  DOI：10.1021/jo982388a

  日期：1999.3.1

  The gem-dialkyl effect has been used to promote the formation of functionalized gamma-lactones in the addition of benzenesulfonyl bromide to diene and enyne esters. Introduction of 3 mol % of pyridine into the reactions increases the yields of lactones produced from tertiary esters. Formation of the C-alpha-C-beta bond of gamma-lactones has been achieved in both C-alpha-->C beta and C-beta-->C-alpha radical cyclization directions.
• Origin of the Diastereoselection in the Indium-Mediated Addition of Haloallylic Sulfones to Aldehydes
  作者：Jae-Hong Min、Se-Young Jung、Bo Wu、Jung Taek Oh、Myoung Soo Lah、Sangho Koo

  DOI：10.1021/ol060297r

  日期：2006.3.1

  The R-1 substituents at C(2) of the haloallylic sulfones 1 play a pivotal role in controlling the diastereoselectivity of the indium-mediated addition reaction to benzalclehyde to produce the homoallylic alcohols 3. The R, Me group of 1 prefers the chair form in the In-coordinated six-membered cyclic transition state to give anti-3a, and the R-1 Ph group of 1 favors the twist boat form to give syn-3n, both in a high 13:1 selectivity.