1-bromohexyl acetate | 145786-99-8

• 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
• 英文名称: 1-bromohexyl acetate
• 英文别名: O-α-bromocarboxylic acid ester
• CAS: 145786-99-8
• 化学式: C₈H₁₅BrO₂
• 分子量: 223.11
• InChiKey: BQRFIKIJKZORFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  220.4±23.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  2-(ethylsulfonyl)-1-nitroethylene 、 1-bromohexyl acetate 在 lithium chloride 、 锌 作用下， 生成 1-pentyl-3-nitro-2-propenyl acetate
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010
• 作为产物：
  描述：

  乙酰溴 、 正己醛 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 以52%的产率得到1-bromohexyl acetate
  参考文献：
  名称：

  手性二烷基甲醇酯的聚合催化不对称合成

  摘要：

  由于手性二烷基甲醇及其衍生酯在有机、药物和生物化学等领域作为中间体和终点具有重要意义，因此开发其不对称合成的有效方法是一项重要的工作。在本报告中，我们描述了一种直接催化对映选择性合成此类酯的方法，从卤代烷（衍生自醛和酰基溴）、烯烃和氢硅烷开始，由镍催化，地球上丰富的金属. 该方法是通用的，可以容忍大小不同并带有一系列官能团的取代基。我们进一步描述了该方法的四组分变体，其中卤代烷是原位生成的，因此无需分离烷基亲电子试剂或烷基金属，同时仍然影响烷基-烷基偶联。最后，我们将我们的收敛方法应用于三种本身具有生物活性或已用于合成生物活性化合物的酯的有效催化对映选择性合成。

  DOI：

  10.1021/jacs.0c01324

文献信息

• Green Access to α-Haloalkyl and α-Halobenzyl Esters, Versatile Intermediates for the One-Pot Two-Step Synthesis of O,O′-Diacyl Acetals Using Zinc-Based Ionic Liquid Catalyst
  作者：Fabienne Fache、Ignasi de Azpiazu、Béatrice Pelotier、Olivier Piva、Christel Gozzi

  DOI：10.1055/s-0037-1612415

  日期：2019.6

  Abstract α-Haloalkyl and α-halobenzyl esters have been synthesized using a zinc-based ionic liquid catalyst, BMIZnCl3. These esters can then react with acids without intermediate purification to obtain mixed O,O′-diacyl acetals in a one-pot process. α-Haloalkyl and α-halobenzyl esters have been synthesized using a zinc-based ionic liquid catalyst, BMIZnCl3. These esters can then react with acids without

  抽象的 已经使用锌基离子液体催化剂BMIZnCl 3合成了α-卤代烷基酯和α-卤代苄基酯。然后，这些酯可以与酸反应而无需中间纯化，得到混合ø，ö '-diacyl缩醛在一个单釜法。 已经使用锌基离子液体催化剂BMIZnCl 3合成了α-卤代烷基酯和α-卤代苄基酯。然后，这些酯可以与酸反应而无需中间纯化，得到混合ø，ö '-diacyl缩醛在一个单釜法。
• 一种配体接力策略促进的镍氢催化烯烃迁移不对称官能团化的方法
  申请人：南京大学

  公开号：CN112939750B

  公开（公告）日：2022-05-17

  本发明公开了一种配体接力策略促进的镍氢催化烯烃迁移不对称官能团化的方法。在金属镍盐、非手性配体、手性配体、碱、氢源、添加剂等作用下，使烯烃分别和多种亲电试剂溶于有机溶剂中进行反应，得到区域选择性和对映选择性优秀的手性化合物。本发明方法可高效合成含多种官能团的手性化合物且产物具有高对映选择性，该方法原料简单易得，操作简便。
• NOVEL CYCLOALKANE ALDEHYDES, METHOD FOR PREPARING SAME, AND USE THEREOF IN THE PERFUME INDUSTRY
  申请人：V. Mane Fils

  公开号：US20140221503A1

  公开（公告）日：2014-08-07

  The invention relates to a compound of general formula I represented below: wherein: R1, R2 and R3 each independently represent a hydrogen atom or saturated or unsaturated, branched or non-branched C1 to C5 alkyl group; m is an integer between 1 and 4; n is an integer between 2 and 4; characterised in that the ring is saturated and comprises from 5 to 8 carbons, that the total number of carbons of the ring and of the radicals R1, R2 and R3 is between 7 and 11 and it being understood that said compound of formula (I) is not: 6-cycloheptylidenehexanal 4-(4-methylcyclohexylidene)-butanal 4-(4-tert-butylcyclohexylidene)-butanal 4-(3,3,5-trimethylcyclohexylidene)-butanal as well as a method of synthesising said compounds, and their uses in perfumery.

  本发明涉及一种通式I的化合物，其表示如下： 其中：R1、R2和R3各自独立地表示氢原子或饱和或不饱和的支链或非支链C1至C5烷基；m是1到4之间的整数；n是2到4之间的整数；其特征在于环是饱和的，包含5到8个碳，环和基团R1、R2和R3的总碳数在7到11之间，并且明确地指出，该通式（I）的化合物不是：6-环庚烯基己醛、4-(4-甲基环己烯基)-丁醛、4-(4-叔丁基环己烯基)-丁醛、4-(3,3,5-三甲基环己烯基)-丁醛，以及合成该化合物的方法和其在香料中的用途。
• Preparation of polyfunctional nitro olefins and nitroalkanes using the copper-zinc reagents RCu(CN)ZnI
  作者：Carole Jubert、Paul Knochel

  DOI：10.1021/jo00046a027

  日期：1992.9

  The addition of the copper-zinc reagents RCu(CN)ZnX to a variety of nitro olefins produces polyfunctional nitroalkanes in high yields. The intermediate zinc or copper nitronates can be directly submitted to a Nef reaction (O3,-78-degrees-C) and converted to polyfunctional ketones in a one-pot procedure. The addition of RCu(CN)ZnX to nitro olefins bearing a leaving group (RSO2, RS) in the beta-position provides pure (E)-nitro olefins in excellent yields. The reaction has been applied for the stereoselective preparation of 1,3-nitrodienes and for a Diels-Alder reaction precursor.
• Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu, J. Org. Chem., 58 (1993) N 3, S 588-599
  作者：Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu

  DOI：——

  日期：——