环辛烷羰基氯化物 | 73093-24-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 环辛烷羰基氯化物
• 英文名称: Cyclooctan-carbonsaeurechlorid
• 英文别名: Cyclooctanecarbonyl chloride
• CAS: 73093-24-0
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: JZUOKBJJPAMFHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  环辛烷羰基氯化物 在 lithium aluminium tetrahydride 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 N,N-Dimethyl-cyclooctyl-methylamin-N-oxyd
  参考文献：
  名称：

  Amine Oxides. VIII. Medium-sized Cyclic Olefins from Amine Oxides and Quaternary Ammonium Hydroxides^1,2

  摘要：

  Thermal decompositions of the N-oxides derived from N,N-dimethyl-1-methylcycloalk,lamines II having eight-, nine- and ten-membered rings yield olefin mixtures containing 98.6, 94.0 and 97.5%, respectively, of 1-methylcycloalkenes. Considerable amounts of the trans isomers are formed from the nine- and ten-membered N-oxides. Pyrolyses of the corresponding quaternary hydroxides produce mixtures of methylenecycloalkanes and 1-methylcycloalkenes (predominantly cis), violation of the Hofmann rule being at a maximum in the decomposition of the nine-membered quaternary hydroxide. Importance of relative product stabilities and the operation of non-bonded interactions are discussed as possible explanations for the observed directions of elimination. Thermal decompositions of the N-oxides and quaternary hydroxides of dimethylcycloalkvimethylamines IV containing eight-, nine- and ten-membered rings proceed as expected with formation of the corresponding methylenecycloalkanes.

  DOI：

  10.1021/ja01502a053
• 作为产物：
  描述：

  环辛烷羧酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 环辛烷羰基氯化物
  参考文献：
  名称：

  四酰基丙二醇酯催化重氮乙酰基环烷烃分解的不寻常产物

  摘要：

  重氮基乙酰基环烷烃的Rh 2（OAc）4辅助分解显示可产生环烷基乙酸（沃尔夫重排），意外的环烷基羧酸和双环酮（分子内CH键插入）。另一方面，Rh 2（OCOCF 3）4促进的反应提供了双环酮和烯酮二聚体。

  DOI：

  10.1016/s0040-4020(97)00507-3

文献信息

• Iridium(i)-catalyzed vinylic C–H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron
  作者：Ikuo Sasaki、Hana Doi、Toshiya Hashimoto、Takao Kikuchi、Hajime Ito、Tatsuo Ishiyama

  DOI：10.1039/c3cc44149k

  日期：——

  Ir(I)-catalyzed C–H borylation of 1-cycloalkenecarboxylic derivatives with bis(pinacolato)diboron affords various alkenylboronates with functional groups in excellent yields. This reaction was also used in a one-pot borylation/Suzuki–Miyaura cross-coupling procedure.

  Ir(I)催化的带有双(频哪醇)二硼的1-环烯羧酸衍生物的C-H硼化反应，以优异的产率得到各种带有功能基团的烯基�硼酸盐。该反应还用于一步法硼化/铃木-宫浦交叉偶联程序。
• Synthesis, biological evaluation, and molecular docking study of sulfonate derivatives as nucleotide pyrophosphatase/phosphodiesterase (NPP) inhibitors
  作者：Mohammad H. Semreen、Mohammed I. El-Gamal、Saif Ullah、Saquib Jalil、Sumera Zaib、Hanan S. Anbar、Joanna Lecka、Jean Sévigny、Jamshed Iqbal

  DOI：10.1016/j.bmc.2019.04.031

  日期：2019.7

  A new series of sulfonate derivatives 1a-zk were synthesized and evaluated as inhibitors of nucleotide pyrophosphatases. Most of the compounds exhibited good to moderate inhibition towards NPP1, NPP2, and NPP3 isozymes. Compound 1m was a potent and selective inhibitor of NPP1 with an IC50 value of 0.387 ± 0.007 µM. However, the most potent inhibitor of NPP3 was found as 1x with an IC50 value of 0.214 ± 0

  合成了一系列新的磺酸盐衍生物1a-zk，并将其评估为核苷酸焦磷酸酶的抑制剂。大多数化合物对NPP1，NPP2和NPP3同工酶表现出良好至中度的抑制作用。化合物1m是一种有效的选择性NPP1抑制剂，IC50值为0.387±0.007 µM。但是，发现最有效的NPP3抑制剂为1x，IC50值为0.214±0.012 µM。此外，化合物1e是NPP2活性最高的抑制剂，IC50值为0.659±0.007 µM。进行了最有效化合物的对接研究，计算结果支持了体外结果。
• Antiproliferative activity of cycloalkanecarboxamide derivatives possessing sulfonate or sulfamate moiety
  作者：Mohammed I. El-Gamal、Hany A. Omar、Mohammad H. Semreen、Israa A. Younes、Youmna Y. Zaghloul、Ayat E. Abbas、Iman G. Moussa、Fatima Hersi、Chang-Hyun Oh

  DOI：10.1016/j.bioorg.2020.103677

  日期：2020.4

  A series of cycloalkanecarboxamide-containing sulfonate and sulfamate derivatives were prepared, and their antiproliferative activity was tested against NCI-60 cancer cell lines panel. Compound 1f possessing cyclohexyl and p-(tert-butyl)benzenesulfonate moieties was the most active among all the target compounds. It exerted broad-spectrum anticancer activity against all the nine cancer types involved

  制备了一系列含环烷甲酰胺的磺酸盐和氨基磺酸盐衍生物，并测试了它们对NCI-60癌细胞系的抗增殖活性。在所有目标化合物中，具有环己基和对-（叔丁基）苯磺酸酯部分的化合物1f活性最高。它对NCI-60研究小组涉及的所有九种癌症类型均具有广谱抗癌活性。此外，含有环己基和对氟苯磺酸盐部分的化合物1g对HT29结肠癌细胞系（IC50 = 4.73 µM）最有效，对HT29的选择性指数比正常成纤维细胞高4.23倍。它通过诱导凋亡（增加caspase 3/7活性）而不是坏死发挥对HT29的抗增殖活性。
• An efficient synthesis and acylation of α-amino-β-keto-esters: Versatile intermediates in the synthesis of peptide mimetics.
  作者：Jasbir Singh、Thomas D. Gordon、William G. Earley、Barry A. Morgan

  DOI：10.1016/s0040-4039(00)60549-x

  日期：1993.1

  A flexible and high yield synthesis of α-amino-β-keto esters has been developed via acylation of the ketimine derivatives of α-amino esters. These α-amino-β-keto-esters were acylated with chiral amino acid derivatives in 36–95% yields.

  通过酰化α-氨基酯的酮亚胺衍生物，已经开发了一种灵活且高产率的α-氨基-β-酮酯的合成方法。这些α-氨基-β-酮基酯被手性氨基酸衍生物酰化，收率为36-95％。
• Facile preparation of thiol esters from organotin mercaptides and acyl chlorides
  作者：David N. Harpp、T. Aida、T.H. Chan

  DOI：10.1016/s0040-4039(01)86433-9

  日期：——

  Organotin mercaptides condense with acyl chlorides to give thiol esters in excellent yield. Of note are efficient syntheses of -butyl and phenyl thiol esters.

  有机锡硫醇盐与酰氯缩合，以优异的收率得到硫醇酯。值得注意的是-丁基和苯基硫醇酯的有效合成。