9-氯-1-壬烯 | 872-06-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 9-氯-1-壬烯
• 中文别名: 9氯1壬烯
• 英文名称: 9-Chlor-nonen-1
• 英文别名: 8-nonen-1-yl chloride；1-Nonene, 9-chloro-；9-chloronon-1-ene
• CAS: 872-06-0
• 化学式: C₉H₁₇Cl
• 分子量: 160.687
• InChiKey: AJGQFZNQNJVFQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  10
• 可旋转键数：
  7
• 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

安全信息

• 海关编码：
  2914700090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  9-氯-1-壬烯 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以87%的产率得到10-碘-1-癸烯
  参考文献：
  名称：

  Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells

  摘要：

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

  DOI：

  10.1021/jm2001053
• 作为产物：
  描述：

  1-溴-6-氯己烷 在 copper(l) iodide 、 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以55%的产率得到9-氯-1-壬烯
  参考文献：
  名称：

  烯丙基硼酯与1°/ 2°/ 3°卤代烷烃的铜催化交叉偶联反应

  摘要：

  首次开发了烯丙基硼酸酯与1°/ 2°/ 3°卤代烷烃在铜存在下的交叉偶联反应，这为构建饱和C（sp 3）–C（sp 3）键。该方案在温和条件下与未活化的伯，仲，甚至叔卤代烷烃显示出优异的相容性。

  DOI：

  10.1021/acs.orglett.5b01612

文献信息

• [EN] USE OF SOLUBLE METAL SALTS IN METATHESIS REACTIONS<br/>[FR] UTILISATION DE SELS MÉTALLIQUES SOLUBLES DANS DES RÉACTIONS DE MÉTATHÈSE
  申请人：MATERIA INC

  公开号：WO2014152309A1

  公开（公告）日：2014-09-25

  The present invention describes the use of soluble metal salts to reduce impurities and metathesis catalysts poisons from olefinic feedstocks to improve olefin metathesis efficiency. The soluble metal salts were added to the olefinic feedstocks to prevent peroxides and catalyst poisons from inhibiting the metathesis catalyst. The soluble metal salts remain in the olefinic feedstocks and are used without further purification in the olefin metathesis reactions. The key to this invention is the soluble metal salt compounds do not inhibit the olefin metathesis catalysts but unexpectedly increase olefin metathesis catalyst efficiency while prior art heterogeneous metal complexes sequester the olefin metathesis catalyst, preventing olefin metathesis.

  本发明描述了利用可溶性金属盐来减少烯烃原料中的杂质和醚交换催化剂毒物，以提高烯烃醚交换效率。可溶性金属盐被添加到烯烃原料中，以防止过氧化物和催化剂毒物抑制醚交换催化剂。这些可溶性金属盐留在烯烃原料中，在烯烃醚交换反应中无需进一步纯化即可使用。这项发明的关键在于可溶性金属盐化合物不会抑制烯烃醚交换催化剂，而是意外地提高了烯烃醚交换催化剂的效率，而传统的异质金属络合物会固定烯烃醚交换催化剂，从而阻止烯烃醚交换。
• Metathesis syntheses of pheromones or their components
  申请人：——

  公开号：US20020022741A1

  公开（公告）日：2002-02-21

  The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R, 6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9, Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.

  本发明涉及对昆虫性诱素或其组分进行交换合成，如E-5-癸烯醇醋酸酯，桃枝蠕蛾性信息素的主要成分；（5R, 6S）-6-乙酰氧基-5-十六醇内酯，蚊子产卵引诱素；E9, Z11-癸二烯醛，山核桃果蛾性信息素；9-十四烯酸甲酯，菜青虫性信息素的类似物；11-十四烯醇醋酸酯，杂食卷叶蛾性信息素；E-4-十三烯醇醋酸酯，番茄针孔螟性信息素的主要成分；E,E-8,10-十二二烯醇，苹果蛾性信息素。这些合成通常采用I-IV类交换催化剂，步骤较少，使用通常易得的起始物质，并具有相对较短的工艺时间。这些合成产量良好，无需昂贵或复杂的设备。该发明还提供了通过交叉交换α-Ω-二乙酰基烯烃和α-Ω-二卤代烃来产生Ω-卤代烯醇的廉价途径，后者可以在传统的氢化方法下轻松转化为Ω-卤代烷醇。
• SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES
  申请人：California Institute of Technology

  公开号：US20130231499A1

  公开（公告）日：2013-09-05

  The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

  本发明涉及一种利用烯烃交换催化剂从廉价、易获得的起始材料合成昆虫信息素，特别是鳞翅目昆虫信息素及其前体和衍生物的方法。
• Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Improved Catalysts for Ethenolysis Reactions
  申请人：Marx Vanessa M.

  公开号：US20140309433A1

  公开（公告）日：2014-10-16

  Described herein are compounds and methods of catalyzing ethenolysis reactions, optionally on an industrial scale. In certain embodiments, the catalysts bear cyclic alkyl amino carbene (CAAC) ligands with an ortho substituent, such as a methyl substituent, on an N-aryl ring. When used to catalyze ethenolysis reactions, certain such compounds produce a turnover number greater than 50,000.

  本文描述了化合物和催化乙烯裂解反应的方法，可选择在工业规模上进行。在某些实施例中，催化剂带有带有一个N-芳基环上的一个类环烷基氨基甲烷（CAAC）配体的邻位取代基，例如一个甲基取代基。当用于催化乙烯裂解反应时，某些这样的化合物产生的周转次数大于50,000。
• Biologically active compounds by catalytic olefin metathesis
  申请人：Bend Research, Inc.

  公开号：US05916983A1

  公开（公告）日：1999-06-29

  Biologically active compounds such as pheromones and precursors thereof are produced by catalyzed cross metathesis of dissimilar terminal olefins or of a cyclodiene and a terminal olefin.

  生物活性化合物，如信息素及其前体，是通过不同末端烯烃或环戊二烯和末端烯烃的催化交叉重聚而产生的。