5-(chloromethyl)nonane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 5-(chloromethyl)nonane
• 英文别名: 5-(Chloromethyl)nonane
• 化学式: C₁₀H₂₁Cl
• 分子量: 176.73
• InChiKey: ZWZDKOAZDDGDOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  氯碘甲烷 、 5-壬酮 在 methyllithium lithium bromide 、 三叔丁基硅烷 、 三(五氟苯基)硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.75h， 以92%的产率得到5-(chloromethyl)nonane
  参考文献：
  名称：

  化学选择性的同源脱氧策略，能够使羰基直接转化为（n + 1）-卤代甲基-烷烃。

  摘要：

  据报道，将类胡萝卜素和氢化物顺序安装在羰基上，提供了卤代甲基烷基衍生物。尽管在与以碳为中心的亲电子试剂的反应中使用类胡萝卜素作为亲核试剂，sp 3型烷基卤化物仍然是用于选择性一碳同系物的难以捉摸的材料。我们的策略是利用羰基化合物作为起始原料，从而能够均匀地实现高收率和化学控制。该策略是灵活的，不仅限于类胡萝卜素。而且，各种类似碳负离子的物种可以充当亲核试剂，因此使其具有普遍的适用性。

  DOI：

  10.1021/acs.orglett.0c02831

文献信息

• SYNTHESIS OF CYCLIC CARBONATES
  申请人：North Michael

  公开号：US20110015409A1

  公开（公告）日：2011-01-20

  A dimeric aluminium(salen) catalyst of formula I: wherein: Y-Q is CR C1 ═N or CR C1 R C2 —NR N1 , where R C1 , R C2 and R N1 are independently selected from H, halo, optionally substituted C 1-20 alkyl, optionally substituted C 5-20 aryl, ether and nitro; each of the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 , is independently selected from H, halo, optionally substituted C 1-20 alkyl, optionally substituted C 5-20 aryl, optionally substituted C 3-20 heterocyclyl, ether and nitro; X 1 and X 2 are independently either (i) a C 2-5 alkylene chain, which is optionally substituted by one or more groups selected from C 1-4 alkyl and C 5-7 aryl, or a C 1-3 bisoxyalkylene chain, which is optionally substituted by one or more groups selected from C 1-4 alkyl and C 5-7 aryl or (ii) represent a divalent group selected from C 5-7 arylene, C 5-7 cyclic alkylene and C 3-7 heterocyclylene, which may be optionally substituted; (i) (a) at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 is selected from L-A, where L is a single bond or a C 1-10 alkylene group and A is an ammonium group paired with a counterion selected from Cl, Br and I; and/or (b) at least one of X 1 and X 2 is a divalent C 3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen atom paired with a counterion selected from Cl, Br and I; and/or (c) at least one of X 1 and X 2 is a C 2-5 alkylene chain or a C 1-3 bisoxyalkylene chain, substituted by a group -Q-L-A, where Q is either —C(═O)—O—, —C(═O)—NH—, or a single bond; and/or (ii) (a) one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 is L-A′, where L is as defined above and A′ is a ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (b) one of X 1 and X 2 is a divalent C 3-7 heterocyclene group, containing a ring atom which is a quaternary nitrogen forming part of an ammonium linking group bound to a solid support and paired with a counterion selected from Cl, Br and I; or (c) one of X 1 and X 2 is a C 2-5 alkylene chain or a C 1-3 bisoxyalkylene chain, substituted by a group -Q-L-A′.

  化学式I的二聚铝(salen)催化剂：其中：Y-Q为CRC1═N或CRC1RC2—NRN1，其中RC1、RC2和RN1独立选择自H、卤素、可选取代的C1-20烷基、可选取代的C5-20芳基、醚和硝基；每个取代基R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16独立选择自H、卤素、可选取代的C1-20烷基、可选取代的C5-20芳基、可选取代的C3-20杂环基、醚和硝基；X1和X2独立选择自(i) C2-5烷基链，可选取自C1-4烷基和C5-7芳基中的一个或多个基团，或C1-3双氧杂烷基链，可选取自C1-4烷基和C5-7芳基中的一个或多个基团；或(ii)代表选自C5-7芳基、C5-7环烷基和C3-7杂环烷基的二价基团，可选取代；(i)(a) R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中至少一个选择自L-A，其中L为单键或C1-10烷基，A为与Cl、Br和I中选择的一个对离子配对的铵基；和/或(b) X1和X2中至少一个为含有一个季铵对离子选择自Cl、Br和I的四价氮原子的C3-7杂环烷基；和/或(c) X1和X2中至少一个为被-Q-L-A取代的C2-5烷基链或C1-3双氧杂烷基链，其中Q为—C(═O)—O—、—C(═O)—NH—或单键；和/或(ii)(a) R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16中的一个为L-A′，其中L如上定义，A′为与Cl、Br和I中选择的一个对离子配对的铵连接基；或(b) X1和X2中的一个为含有一个季铵对离子选择自Cl、Br和I的四价氮原子的C3-7杂环烷基，形成与固体支持物相连的铵连接基；或(c) X1和X2中的一个为被-Q-L-A′取代的C2-5烷基链或C1-3双氧杂烷基链。
• Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (<i>n+1</i>)-Halomethyl-Alkanes
  作者：Margherita Miele、Andrea Citarella、Thierry Langer、Ernst Urban、Martin Zehl、Wolfgang Holzer、Laura Ielo、Vittorio Pace

  DOI：10.1021/acs.orglett.0c02831

  日期：2020.10.2

  The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high

  据报道，将类胡萝卜素和氢化物顺序安装在羰基上，提供了卤代甲基烷基衍生物。尽管在与以碳为中心的亲电子试剂的反应中使用类胡萝卜素作为亲核试剂，sp 3型烷基卤化物仍然是用于选择性一碳同系物的难以捉摸的材料。我们的策略是利用羰基化合物作为起始原料，从而能够均匀地实现高收率和化学控制。该策略是灵活的，不仅限于类胡萝卜素。而且，各种类似碳负离子的物种可以充当亲核试剂，因此使其具有普遍的适用性。