(2E)-6-Bromo-2,6-heptadien-1-ol | 137609-79-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (2E)-6-Bromo-2,6-heptadien-1-ol
• 英文别名: (2E)-6-bromohepta-2,6-dien-1-ol
• CAS: 137609-79-1
• 化学式: C₇H₁₁BrO
• 分子量: 191.068
• InChiKey: XVDPXFZUSQDFFI-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-6-Bromo-2,6-heptadien-1-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 palladium diacetate 、 三丁基膦 、 三苯基膦 N-甲基吗啉 、 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 甲酸 、 草酰氯 、 二甲基硫 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 硒脲酸 、 sodium hydride 、 magnesium sulfate 、 potassium carbonate 、 sodium fluoride 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.33h， 生成 <3S-(1E,3α,5β)>-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid ethyl ester
  参考文献：
  名称：

  An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthon

  摘要：

  Chiral synthesis of the A-ring synthon 3 of 1alpha,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1alpha,25-dihydroxyvitamin D3 (1a) was obtained.

  DOI：

  10.1021/jo00061a028
• 作为产物：
  描述：

  tert-Butyl 4-bromo-4-pentenoate 在 aluminum oxide 、 lithium aluminium tetrahydride 、 sodium hydride 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 (2E)-6-Bromo-2,6-heptadien-1-ol
  参考文献：
  名称：

  Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes

  摘要：

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.

  DOI：

  10.1021/jo00072a030

文献信息

• Stereoselective synthesis of 1α-hydroxyvitamin D3 A-ring synthons by palladium-catalyzed cyclization
  作者：Kazuo Nagasawa、Yoshiro Zako、Hideki Ishihara、Isao Shimizu

  DOI：10.1016/s0040-4039(00)93501-9

  日期：1991.9

  Palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates proceeded stereoselectively to give 1-alpha-hydroxyvitamin D3 A-ring synthons in good yields.
• Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes
  作者：G. Davis Harris、R. Jason Herr、Steven M. Weinreb

  DOI：10.1021/jo00072a030

  日期：1993.9

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.
• An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthon
  作者：Kazuo Nagasawa、Hideki Ishihara、Yoshiro Zako、Isao Shimizu

  DOI：10.1021/jo00061a028

  日期：1993.4

  Chiral synthesis of the A-ring synthon 3 of 1alpha,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1alpha,25-dihydroxyvitamin D3 (1a) was obtained.