3-cyano-1,1-dimethyl-2-bis(trifluoromethyl)-1-azonia-2-boratacyclopentane | 185526-29-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 3-cyano-1,1-dimethyl-2-bis(trifluoromethyl)-1-azonia-2-boratacyclopentane
• CAS: 185526-29-8
• 化学式: C₈H₁₁BF₆N₂
• 分子量: 259.99
• InChiKey: XYMCFLHLMBEQRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-cyano-1,1-dimethyl-2-bis(trifluoromethyl)-1-azonia-2-boratacyclopentane 在 iBu₂AlH 、 aq. HCl 作用下， 以 盐酸 、 二氯甲烷 为溶剂， 以70%的产率得到2,2-bis(trifluoromethyl)-1,1-dimethyl-3-formyl-1-azonia-2-boratacyclopentane
  参考文献：
  名称：

  Reactions of (CF ₃ ) ₂ BNMe ₂ with ω‐Halonitriles — Crystal and Molecular Structure of [ cyclo ‐C ₃ H ₄ (CN)](CF ₃ ) ₂ B·NHMe ₂

  摘要：

  AbstractDimethylaminobis(trifluoromethyl)borane, (CF3)2BNMe2 (A), reacts with Cl(CH2)3CN to yield [Cl(CH2)2CH(CN)](CF3)2B·NHMe2 (1) whereas Br(CH2)3CN and A combine in a 1:2 ratio to form [cyclo‐C3H4(CN)](CF3)2B·NHMe2 (2) and Br(CF3)2B·NHMe2. Br(CH2)nCN and A yield [Br(CH2)n‐1 CH‐(CN)](CF3)2B·NHMe2, n=4 (3), n=5 (4) and n=6 (5). Compound 2 and (NCCH2)CF3)2B·NHMe2 can be alkylated at nitrogen with CH3I/KOH in ether to yield [cyclo‐C3H4(CN)]‐(CF3)2B·NMe3 (6) and (NCCH2)(CF3)2B·NMe3 (7), respectively. treatment of 1 and 3 with hydroxide in ether gives the respective five‐ and six‐membered heterocycles (CF3)2 (8) and (9). Reduction of the nitrile group with (iBu)2Alh in CH2Cl2 at –50°C followed by hydrolysis furnishes the corresponding aldehydes (OCHCH2) (CF3)2B·NMe3 (10), [cyclo‐C3H4(CHO)](CF3)2B·NMe3 (11) and (12). The structure of 2 was determined by an X‐ray investigation.

  DOI：

  10.1002/cber.19961291222
• 作为产物：
  描述：

  (3-chloro-1-cyanopropyl)bis(trifluoromethyl)borane-dimethylamine 在 KOH 作用下， 以 乙醚 为溶剂， 以90%的产率得到3-cyano-1,1-dimethyl-2-bis(trifluoromethyl)-1-azonia-2-boratacyclopentane
  参考文献：
  名称：

  Reactions of (CF ₃ ) ₂ BNMe ₂ with ω‐Halonitriles — Crystal and Molecular Structure of [ cyclo ‐C ₃ H ₄ (CN)](CF ₃ ) ₂ B·NHMe ₂

  摘要：

  AbstractDimethylaminobis(trifluoromethyl)borane, (CF3)2BNMe2 (A), reacts with Cl(CH2)3CN to yield [Cl(CH2)2CH(CN)](CF3)2B·NHMe2 (1) whereas Br(CH2)3CN and A combine in a 1:2 ratio to form [cyclo‐C3H4(CN)](CF3)2B·NHMe2 (2) and Br(CF3)2B·NHMe2. Br(CH2)nCN and A yield [Br(CH2)n‐1 CH‐(CN)](CF3)2B·NHMe2, n=4 (3), n=5 (4) and n=6 (5). Compound 2 and (NCCH2)CF3)2B·NHMe2 can be alkylated at nitrogen with CH3I/KOH in ether to yield [cyclo‐C3H4(CN)]‐(CF3)2B·NMe3 (6) and (NCCH2)(CF3)2B·NMe3 (7), respectively. treatment of 1 and 3 with hydroxide in ether gives the respective five‐ and six‐membered heterocycles (CF3)2 (8) and (9). Reduction of the nitrile group with (iBu)2Alh in CH2Cl2 at –50°C followed by hydrolysis furnishes the corresponding aldehydes (OCHCH2) (CF3)2B·NMe3 (10), [cyclo‐C3H4(CHO)](CF3)2B·NMe3 (11) and (12). The structure of 2 was determined by an X‐ray investigation.

  DOI：

  10.1002/cber.19961291222

文献信息

• Fluorine effects in organoboranes; formation of cyanoalkyl-bis(trifluoromethyl)-organoborates
  作者：David J. Brauer、Gottfried Pawelke

  DOI：10.1016/s0022-1139(99)00102-5

  日期：1999.9

  protonation yields the zwitterions R–B(CF3)2–CH(CN)–CH2–CH2–NHMe2 (R=Bu (4a), tBu (4b) and Ph (4c)). Zwitterions with R=C3H7CC (4d) or PhCC (4e) are formed by the reaction of 3 with tBuLi in the presence of C3H7CCH or PhCCH. BrCH(CN)(F3C)2B·NHMe2 (5), which has been obtained from (F3C)2BNMe2 and BrCH2CN, forms on treatment with LiOH×H2O/ether HOB(CF3)2–CH(CN)–NHMe2 (6). The structure of 6 has been investigated

  研究了三烷基胺双（三氟甲基）硼烷（F 3 C）2 R 1 B·NR 3与强碱的反应。（F 3 C）2 EtB·NMe 3用t BuLi处理时形成氮基，而（F 3 C）2（NCCH 2）B·NMe 3用KOH /醚自发消除三甲胺，形成羟基硼酸酯K [（F 3 C）2（NCCH 2）BOH]（1a）。（F 3 C）2（NCCH 2）B·NMe 3与t BuLi / thf或PhLi / thf反应生成Li [（F 3 C）2（NCCH 2）B t Bu]（1b'）或Li [（F 3 C）2（NCCH 2）BPh]（1c'），但在存在CH 3 CN的情况下，与t BuLi / thf的反应导致Li [（F 3 C）2（NCCH 2）2 B]（1d'）的形成。锂盐1b' - 1d'被转化为相应的Cs盐1b - 1d使用阳离子交换树脂。反式-H 3 C–CHCH–CH（CN）（F 3 C）2 B·NHMe
• Reactions of (CF ₃ ) ₂ BNMe ₂ with ω‐Halonitriles — Crystal and Molecular Structure of [ <i>cyclo</i> ‐C ₃ H ₄ (CN)](CF ₃ ) ₂ B·NHMe ₂
  作者：David J. Brauer、Hans Bürger、Thomas Dittmar、Gottfried Pawelke

  DOI：10.1002/cber.19961291222

  日期：1996.12

  AbstractDimethylaminobis(trifluoromethyl)borane, (CF3)2BNMe2 (A), reacts with Cl(CH2)3CN to yield [Cl(CH2)2CH(CN)](CF3)2B·NHMe2 (1) whereas Br(CH2)3CN and A combine in a 1:2 ratio to form [cyclo‐C3H4(CN)](CF3)2B·NHMe2 (2) and Br(CF3)2B·NHMe2. Br(CH2)nCN and A yield [Br(CH2)n‐1 CH‐(CN)](CF3)2B·NHMe2, n=4 (3), n=5 (4) and n=6 (5). Compound 2 and (NCCH2)CF3)2B·NHMe2 can be alkylated at nitrogen with CH3I/KOH in ether to yield [cyclo‐C3H4(CN)]‐(CF3)2B·NMe3 (6) and (NCCH2)(CF3)2B·NMe3 (7), respectively. treatment of 1 and 3 with hydroxide in ether gives the respective five‐ and six‐membered heterocycles (CF3)2 (8) and (9). Reduction of the nitrile group with (iBu)2Alh in CH2Cl2 at –50°C followed by hydrolysis furnishes the corresponding aldehydes (OCHCH2) (CF3)2B·NMe3 (10), [cyclo‐C3H4(CHO)](CF3)2B·NMe3 (11) and (12). The structure of 2 was determined by an X‐ray investigation.