1-乙酰氧基-7-溴庚烷 | 21727-91-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1-乙酰氧基-7-溴庚烷
• 中文别名: 7-溴-1-庚醇乙酸酯
• 英文名称: 7-bromoheptyl acetate
• 英文别名: 1-acetoxy-7-bromoheptane
• CAS: 21727-91-3
• 化学式: C₉H₁₇BrO₂
• 分子量: 237.137
• InChiKey: YAFBPBCITSMEMS-UHFFFAOYSA-N

物化性质

• 保留指数：
  1477

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-7-溴庚烷 在 sodium hydroxide 、 三丁基膦 、 sodium hydride 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (2-{2-[4-(7-Hydroxy-heptyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl]-ethoxy}-phenyl)-acetic acid
  参考文献：
  名称：

  Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

  摘要：

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm0301888
• 作为产物：
  描述：

  1,7-辛二烯 在 三溴化磷 作用下， 以 吡啶 、 苯 为溶剂， 生成 1-乙酰氧基-7-溴庚烷
  参考文献：
  名称：

  A new stereospecific synthesis of sex pheromones of insects of the (Z)-alkenyl-1-acetate series based on selective ozonolysis of 1-methyl-1Z,5Z-cyclooctadiene

  摘要：

  DOI：

  10.1016/s0040-4039(01)86730-7

文献信息

• Synthesis of 23-, 25-, 27-, and 29-Membered (<i>Z</i>)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization
  作者：Tomoya Iwasaki、Yuka Tajimi、Kenta Kameda、Callum Kingwell、William Wcislo、Kazuyuki Osaka、Mugen Yamawaki、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/acs.joc.9b00870

  日期：2019.6.21

  A new strategy for the synthesis of 23-, 25-, 27-, and 29-membered (Z)-selective unsaturated and saturated macrocyclic lactones from commercially available 16- and 17-membered macrocyclic lactones and bromoalcohols by Wittig reaction, Yamaguchi macrolactonization, and photoinduced decarboxylative radical macrolactonization is described. The position of the unsaturated part in the macrocyclic lactones

  一种新的策略，可通过Wittig反应，山口宏内酯化，由Wittig反应从市售的16和17元大环内酯和溴代醇合成23、25、27和29元（Z）选择性不饱和和饱和大环内酯，并且描述了光诱导的脱羧自由基大内酯化。大环内酯中不饱和部分的位置可以通过改变原料中的碳数来控制。该方案可以从简单的起始原料容易地获得所需的大环（Z）-选择性不饱和和饱和大环内酯。
• Pheromone, XXXII. Bausteine zur Darstellung zweifach ungesättigter Schmetterlings-pheromone
  作者：Hans Jürgen Bestmann、Karl Heinrich Koschatzky、Wilfried Schätzke、Joachim Süß、Otto Vostrowsky

  DOI：10.1002/jlac.198119810920

  日期：1981.9.21

  Die Darstellung α,ω-bifunktioneller Ausgangsverbindungen sowie (Z)- und (E)-konfigurierter, ungesättigter Synthesebausteine, die man mittels Wittig-Reaktion, Michael-Addition, Acetylen-synthese oder Crombie-Reaktion erhält, wird beschrieben. Diese Verbindungen werden im Rahmen eines „Baukastensystems” zur Synthese bisolefinischer Sexualpheromone benötigt.

  描述了通过Wittig反应，Michael加成，乙炔合成或Crombie反应获得的α，ω-双功能起始化合物以及（Z）和（E）构型的不饱和合成结构单元的表示。这些化合物是合成双烯烃性信息素的“模块系统”的一部分。
• Trehan, I. R.; Kad, G. L.; Seth, Vibha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 8, p. 793 - 794
  作者：Trehan, I. R.、Kad, G. L.、Seth, Vibha

  DOI：——

  日期：——
• Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity
  作者：Sadanandan E. Velu、Walter A. Cristofoli、Gabriel J. Garcia、Christie G. Brouillette、Milton C. Pierson、Chi-Hao Luan、Lawrence J. DeLucas、Wayne J. Brouillette

  DOI：10.1021/jm030003x

  日期：2003.7.1

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.
• Metalation reactions. III. Metalation of octadecynols and octadecynyl methyl ethers
  作者：Joseph Klein、E. Gurfinkel

  DOI：10.1021/jo01264a044

  日期：1969.12