3-Brom-hexin-(1) | 49769-87-1

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 3-Brom-hexin-(1)
• 英文别名: 3-Bromohex-1-yne
• CAS: 49769-87-1
• 化学式: C₆H₉Br
• 分子量: 161.041
• InChiKey: DKOSDHKWKUGAKY-UHFFFAOYSA-N

物化性质

• 沸点：
  82-83 °C(Press: 110 Torr)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 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：

  3-Brom-hexin-(1) 在 lithium amide 作用下， 以 氨 为溶剂， 生成 3-ethyl-4-propyl-dec-5-yn-3-ol
  参考文献：
  名称：

  Synth�se d'alcools ac�tyl�niques par alkylation d'hydroxy-?-alkynes-1

  摘要：

  Synthesis of acetylenic alcohols by alkylation of ω‐hydroxy‐1‐alkynesIn liquid ammonia and with lithium amide, the alkylation of an ω‐hydroxyl‐alkyne proceeds with good yield with primary or secondary alcohols and with fair yield with tertiary alcohols. It is a very convenient way to prepare many substituted acetylenic alcohols.

  DOI：

  10.1002/hlca.19780610635
• 作为产物：
  描述：

  甲苯-4-磺酸-(1-丙基-丙-2-炔基酯) 在 lithium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以51%的产率得到3-Brom-hexin-(1)
  参考文献：
  名称：

  Preparation of polyfunctional allenic alcohols by the regioselective addition of functionalized propargylic chromium(III) organometallics to carbonyl compounds

  摘要：

  The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6% of the regioisomeric acetylenic alcohol 4 is formed) and in good yields (68-90%). Interestingly, this method allows the generation of highly functionalized intermediate propargylic chromium organometallics contained an ester, cyano, or chloride functionality. The alpha-alkyl-substituted propargylic bromide 10 reacts with benzaldehyde yielding the acetylenic alcohol 11 as a diastereomeric mixture of only one regioisomer (90% yield).

  DOI：

  10.1021/jo00041a006

文献信息

• Studies on Acetylenic Compounds. XXII. Ring Closure. (4). New Synthesis of Thiazoles and Imidazole.
  作者：Yasuo Yura

  DOI：10.1248/cpb.10.376

  日期：——

  It was found that the compounds having the general formula RCH(X)-C≡C-R'gave thiazole derivatives by reaction with thiourea. The relationship between the structure of thiazoles and substituent groups was clarified as follows : (1) When R=R'=Ph, 2-amino-4-benzyl-5-phenylthiazole (IId) is obtained, (2) When R=alkyl, R'=H, two kinds of thiazoles are obtained ; and (3) when R=R'=alkyl, thiazole derivative is not obtained. Similarly, propargyl bromide and phenylpropargyl bromide, when reacted with ammonium dithiocarbamate, afforded 2-mercapto-4-methylthiazole (XX) and 2-mercapto-4-benzylthiazole (XXIII), respectively. Further, 2-amino-4-methylimidazole (XXV) was obtained from guanidine and propargyl bromide.

  研究发现，具有通式RCH(X)-C≡C-R'的化合物在反应中与硫脲作用生成噻唑衍生物。噻唑结构和取代基之间的关系阐明如下：(1) 当R=R'=Ph时，获得2-氨基-4-苄基-5-苯基噻唑(IId)；(2) 当R=烷基，R'=H时，获得两种噻唑；(3) 当R=R'=烷基时，不生成噻唑衍生物。同样地，炔丙基溴和苯基炔丙基溴与氨荒酸盐反应，分别得到2-巯基-4-甲基噻唑(XX)和2-巯基-4-苄基噻唑(XXIII)。进一步地，从胍和炔丙基溴获得2-氨基-4-甲基咪唑(XXV)。
• Free Radical Addition of Thiophenol to 3-Substituted 1-Alkyne with or without Migration of the Substituents
  作者：Hideyoshi Miyake、Kimiaki Yamamura

  DOI：10.1246/bcsj.61.3752

  日期：1988.10

  Thiophenol reacts with 3-phenylthio- and 3-bromo-1-alkyne in the presence of radical initiator to give 1,2-bis(phenylthio)-1-alkene and 2-bromo-1-phenylthio-1-alkene.

  在自由基引发剂的存在下，硫代苯酚与 3-苯硫基和 3-溴-1-炔烃反应生成 1,2-双（苯硫基）-1-烯烃和 2-溴-1-苯硫基-1-烯烃。
• One-Pot Approach to Installing Eight-Membered Rings onto Indoles
  作者：Can Zhu、Xue Zhang、Xiongdong Lian、Shengming Ma

  DOI：10.1002/anie.201202971

  日期：2012.7.27

  Ring fusion: The Pd0‐catalyzed reaction of 2‐allyl‐3‐iodo‐1‐tosyl‐1H‐indoles and propargylic bromides affords dihydrocycloocta[b]indoles (see scheme; M.S.=molecular sieves, TFP=tris(2‐furyl)phosphine, Ts=4‐toluenemethanesulfonyl), and proceeds by carbon–carbon coupling, [1,5]‐hydrogen migration, and electrocyclization. The newly established method was used to efficiently access iprindole.

  环融合：2-烯丙基-3-碘-1--1-甲苯磺酰基-1 H-吲哚与炔丙基溴的Pd 0催化反应可得到二氢环辛八烯[ b ]吲哚（参见示意图； MS =分子筛，TFP = tris（2−呋喃基膦，Ts = 4-甲苯甲磺酰基），并通过碳-碳偶合，[1,5]-氢迁移和电环化进行。新建立的方法用于有效地访问艾普琳。
• 569. Researches on acetylenic compounds. Part XXI. Reformatsky reactions with propargyl bromides
  作者：H. B. Henbest、E. R. H. Jones、I. M. S. Walls

  DOI：10.1039/jr9490002696

  日期：——
• Moreau,J.-L.; Gaudemar,M., Bulletin de la Societe Chimique de France, 1973, p. 2729 - 2731
  作者：Moreau,J.-L.、Gaudemar,M.

  DOI：——

  日期：——