(R)-1,1-dibromo-3-methyl-1-pentene | 686718-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1,1-dibromo-3-methyl-1-pentene
• 英文别名: (R)-1,1-dibromo-3-methylpent-1-ene；(3R)-1,1-dibromo-3-methylpent-1-ene
• CAS: 686718-84-3
• 化学式: C₆H₁₀Br₂
• 分子量: 241.953
• InChiKey: PPVHYRCRKWRZIP-RXMQYKEDSA-N

物化性质

• 沸点：
  188.9±13.0 °C(Predicted)
• 密度：
  1.637±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (R)-1,1-dibromo-3-methyl-1-pentene 在 正丁基锂 、 二氯二茂锆 、 四丁基氟化铵 、 叔丁基锂 、 三乙基硼氢化锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 various solvents 为溶剂， 反应 6.5h， 生成 (E)-(2R,4S,8R)-2,4,6,8-tetramethyl-6-decen-1-ol
  参考文献：
  名称：

  An improved synthesis of the scyphostatin side-chain

  摘要：

  A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over,six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.156
• 作为产物：
  描述：

  2-甲基丁醇 在 pseudomonas fluorescens lipase 乙酸乙烯酯 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-1,1-dibromo-3-methyl-1-pentene
  参考文献：
  名称：

  An improved synthesis of the scyphostatin side-chain

  摘要：

  A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over,six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.156

文献信息

• Highly (≥98%) Stereo- and Regioselective Trisubstituted Alkene Synthesis of Wide Applicability via 1-Halo-1-alkyne Hydro- boration-Tandem Negishi-Suzuki Coupling or Organoborate Migratory Insertion
  作者：Shiqing Xu、Ching-Tien Lee、Honghua Rao、Ei-ichi Negishi

  DOI：10.1002/adsc.201100420

  日期：2011.11

  synthetic utility of the present methodology has been demonstrated in the highly selective synthesis of side chain (4) of scyphostatin in 28% yield over nine steps in the longest linear sequence from allyl alcohol. Thus, this new tandem protocol has been emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to prepare.

  然后用有机锂或格氏试剂处理以产生具有反向立体构型的三取代烯烃。本方法的合成效用已在从烯丙醇以最长线性序列的九个步骤以 28% 的收率高选择性合成 scyphostatin 的侧链 (4) 中得到证明。因此，这种新的串联方案已成为最广泛适用和高度选择性的三取代烯烃路线，包括那些难以制备的烯烃。
• Macrocyclic Ghrelin Receptor Antagonists and Inverse Agonists and Methods of Using the Same
  申请人：Hoveyda Hamid R.

  公开号：US20110105389A1

  公开（公告）日：2011-05-05

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (GRLN, growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and/or variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as antagonists or inverse agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, obesity and obesity-associated disorders, appetite or eating disorders, addictive disorders, cardiovascular disorders, gastrointestinal disorders, genetic disorders, hyperproliferative disorders, central nervous system disorders and inflammatory disorders.

  本发明提供了新型构象定义的大环化合物，已被证明是生长激素分泌素受体（GRLN，生长激素分泌素受体，GHS-R1a及其亚型、异构体和/或变种）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的拮抗剂或逆向激动剂，以及用于治疗和预防一系列医学疾病，包括但不限于代谢和/或内分泌紊乱、肥胖和与肥胖相关的疾病、食欲或进食紊乱、成瘾紊乱、心血管疾病、胃肠道疾病、遗传疾病、过度增殖性疾病、中枢神经系统疾病和炎症性疾病。
• Marcacci, Fabrizio; Giacomelli, Giampaolo; Menicagli, Rita, Gazzetta Chimica Italiana, 1980, vol. 110, # 2/3, p. 195 - 200
  作者：Marcacci, Fabrizio、Giacomelli, Giampaolo、Menicagli, Rita

  DOI：——

  日期：——
• PROCESS FOR PREPARATION OF (3R)-2,4-DI-LEAVING GROUP-3-METHYLBUT-1-ENE
  申请人：ALPHORA RESEARCH INC.

  公开号：US20140323744A1

  公开（公告）日：2014-10-30

  The specification relates to compounds and process for the preparation of a compound of formula 7, where LG is a leaving group and hal is a halide and is Cl, Br or I. The compound of formula 7 can be useful in the preparation of natural products, such as halichondrin and its derivatives.
• US9181152B2
  申请人：——

  公开号：US9181152B2

  公开（公告）日：2015-11-10