1-bromo-non-3-yne | 31333-14-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-bromo-non-3-yne
• 英文别名: 1-bromo-3-nonyne；1-Brom-non-3-in；1-Brom-3-nonin；1-Bromonon-3-yne；1-bromonon-3-yne
• CAS: 31333-14-9
• 化学式: C₉H₁₅Br
• 分子量: 203.122
• InChiKey: SQUCRGHLFVXKEL-UHFFFAOYSA-N

物化性质

• 沸点：
  219.3±23.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  1-bromo-non-3-yne 在 Lindlar's catalyst lithium hydroxide 、 potassium tert-butylate 、 氧气 、 sodium 2-mercaptoacetate 、 氘 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 生成 (5S)-5-pentyldihydrofuran-2(3H)-one-4-d
  参考文献：
  名称：

  Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids

  摘要：

  (S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

  DOI：

  10.1021/jo00018a001
• 作为产物：
  描述：

  3-壬炔-1-醇 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 1-bromo-non-3-yne
  参考文献：
  名称：

  Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids

  摘要：

  (S)-delta-Decanolide (4) was isolated from cultures of Cladosporium suaveolens after the microorganism was fed either (S)- or (R,S)-coriolic acid (1). Feeding (R,S)-10-hydroxyoctadec-(8E)-enoic acid (2) to Yarrowia lipolytica produced (S)-gamma-dodecanolide. When (S)-homocoriolic acid (3) was fed to C.suaveolens, gamma-nonalide slightly enriched in the S enantiomer was produced. At some stage in the biodegradation of 3, an inversion of configuration, from S to R, occurred and was accompanied by the loss of the hydrogen atom originally present on C-14, as GLC/MS analysis of the products of feeding C. suaveolens with dideuterated 10 showed.

  DOI：

  10.1021/jo00018a001

文献信息

• Synthesis of<i>cis</i>-12-Nonadecen-9-one,<i>cis</i>-13-Icosen-10-one, the Pheromone of Peach Fruit Moth, and<i>cis</i>-15-Henicosen-11-one, the Pheromone of Douglas Fir Tussock Moth
  作者：Shota Ito、Norio Saito、Kiyotaka Hatakeda、Tomio Goto、Yutaka Ikushima、Takashi Asano

  DOI：10.1246/bcsj.57.2015

  日期：1984.7

  A convenient synthesis of cis-12-nonadecen-9-one (4a), cis-13-icosen-10-one (4b), the pheromone of peach fruit moth, and cis-15-henicosen-11-one (4c), the pheromone of Douglas fir tussock moth, is described. 4a was synthesized from methyl 3-oxoundecanoate and 1-bromo-2-nonyne (2a) via 12-nonadecyn-9-one. The higher homo-log 4b could be obtained from methyl-3-oxododecanoate and 2a. Similarly, 4c was

  cis-12-nonadecen-9-one (4a)、cis-13-icosen-10-one (4b)、桃果蛾信息素和cis-15-henicosen-11-one (4c)的便捷合成描述了花旗松草蛾的信息素。4a 是由 3-氧代十一酸甲酯和 1-溴-2-壬炔 (2a) 通过 12-nonadecyn-9-one 合成的。更高的同系物 4b 可以从 3-氧代十二酸甲酯和 2a 中获得。类似地，4c 由 3-氧代十三酸甲酯和 1-溴-3-壬炔 (2b) 制备。
• A General Catalyst for Site-Selective C(sp³)–H Bond Amination of Activated Secondary over Tertiary Alkyl C(sp³)–H Bonds
  作者：Ryan J. Scamp、James G. Jirak、Nicholas S. Dolan、Ilia A. Guzei、Jennifer M. Schomaker

  DOI：10.1021/acs.orglett.6b01392

  日期：2016.6.17

  catalyst-controlled and selective carbon–hydrogen (C–H) bond amination of activated secondary C–H bonds over tertiary alkyl C(sp3)–H bonds is challenging, as substrate control often dominates when reactive nitrene intermediates are involved. In this letter, we report the design of a new silver complex, [(Py5Me2)AgOTf]2, that displays general and good-to-excellent selectivity for nitrene insertion into

  作为底物控制，发现能够促进活化的二级 C-H 键在叔烷基 C(sp 3 )-H 键上的一般、催化剂控制和选择性碳-氢 (C-H) 键胺化的过渡金属配合物的发现具有挑战性当涉及反应性氮烯中间体时，通常占主导地位。在这封信中，我们报告了一种新的银配合物 [(Py 5 Me 2 )AgOTf] 2的设计，该配合物在将氮烯插入炔丙基、苄基和烯丙基 C-H 键时表现出普遍和良好的选择性。叔烷基 C(sp 3 )-H 键。
• The synthesis of a leukotriene with SRS-like activity
  作者：Joshua Rokach、Yves Girard、Yvan Guindon、Joseph G. Atkinson、Marie Larue、Robert N. Young、Paul Masson、George Holme

  DOI：10.1016/s0040-4039(00)92753-9

  日期：1980.1
• Bachman, Journal of the American Chemical Society, 1935, vol. 57, p. 383
  作者：Bachman

  DOI：——

  日期：——
• Cellular uptake of a catechol iron chelator and chloroquine into Plasmodium falciparum infected erythrocytes
  作者：Akli Hammadi、Florence Ramiandrasoa、Veronique Sinou、Christophe Rogier、Thierry Fusai、Jacques Le Bras、Daniel Parzy、Gerhard Kunesch、Bruno Pradines

  DOI：10.1016/s0006-2952(03)00042-x

  日期：2003.4

  Our study demonstrates the capacity of FR160, a catechol iron chelator, to reach and accumulate into infected Plasmodium falciparum erythrocytes and parasites (cellular accumulation ratio between 12 and 43). Steady-state FR160 accumulation is obtained after 2 hr of exposure. After 2 hr exposure, it reaches intracellular levels that are 4- to 10-fold higher in infected red blood cells than those attained in normal erythrocytes. There is quite a good correlation between the accumulation of chloroquine and FR160 in the different strains (r = 0.939) and in the IC50 values (r = 0.719). In contrast, the accumulation of FR160 and its activity is poorly correlated (r = 0.500), suggesting that activity of FR160 may be independent of its penetration into infected erythrocytes. The mechanism of accumulation is yet unknown but based on inhibitor studies, the uptake of FR160 seems to be not associated with the calcium pump or channel, the potassium channel or the Na+/H+ exchanger. Combinations of FR160 with verapamil, diltiazem, clotrimazole, amiloride, diazoxide, 4-aminopyridine, and picrotoxin should be avoided (antagonistic effects). The potent in vitro activity of FR160 on chloroquine-resistant strains or isolates, its lower toxicity against Vero cells, its mechanisms of action, its capacity to reach rapidly and accumulate into infected erythrocytes suggest that FR160 holds much promise as a new structural lead and effective antimalarial agent or at least a promising adjuvant in treatment of malaria. (C) 2003 Elsevier Science Inc. All rights reserved.