trans-2-Bromo-1-<(trifluoromethanesulfonyl)oxy>cyclohexane | 83294-08-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trans-2-Bromo-1-<(trifluoromethanesulfonyl)oxy>cyclohexane
• 英文别名: trans-1-bromo-2-(trifluoromethanesulfonyloxy)cyclohexane；trans-2-bromocyclohexane-1-trifluoromethanesulfonate；trans-2-bromocyclohexyl trifluoromethanesulfonate；[(1R,2R)-2-bromocyclohexyl] trifluoromethanesulfonate
• CAS: 83294-08-0
• 化学式: C₇H₁₀BrF₃O₃S
• 分子量: 311.12
• InChiKey: UTCXSBZBOWUXOR-PHDIDXHHSA-N

物化性质

• 沸点：
  280.2±40.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-2-Bromo-1-<(trifluoromethanesulfonyl)oxy>cyclohexane 以0%的产率得到
  参考文献：
  名称：

  Zheng C. Y., Slebocka-Tilk H., Nagorski R. W., Alvarado L., Brown R. S., J. Org. Chem., 58 (1993) N 8, S 2122-2127

  摘要：

  DOI：
• 作为产物：
  描述：

  环己烯 在 trifluoromethanesulfonate 、 溴 作用下， 生成 trans-1,2-dibromocyclohexane 、 trans-2-Bromo-1-<(trifluoromethanesulfonyl)oxy>cyclohexane
  参考文献：
  名称：

  Zefirov, N. S.; Koz'min, A. S.; Sorokin, V. D., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1546 - 1547

  摘要：

  DOI：

文献信息

• Mechanistic Evaluation of the Transfer of Br⁺ from Bis<i>(sym</i>-collidine)bromonium Triflate to Acceptor Alkenes
  作者：Alexei A. Neverov、R. S. Brown

  DOI：10.1021/jo980627o

  日期：1998.8.1

  4-penten-1-ol with the reactive intermediate coll-Br(+) are fast but not very sensitive to the nature of the nucleophile, the second-order rate constants being 3 x 10(6), 1.1 x 10(6), 1.5 x 10(5), and 4.5 x 10(4) M(-)(1) s(-)(1), respectively. (1)H NMR analysis of the reaction of trans-1-bromo-2(trifluoromethanesulfonyl)cyclohexane, produced in situ from cyclohexene and 2-Br(+)/OTf(-) in CD(2)Cl(2), with tetrabutylammonium

  三氟甲磺酸双（对称-可力丁）溴化铵（2-Br（+）/ OTf（-））与金刚烷金刚烷（Ad = Ad），4-戊烯-1-醇（4）和环己烯的反应动力学在各种条件下于25°C下于1,2-二氯乙烷中进行了研究。显示所有反应的速率均受添加的可力丁抑制，表明所有步骤的第一步是将2-Br（+）/ OTf（-）可逆解离为游离可力丁和反应性中间体coll-Br（ +），然后被烯烃捕获。Ad = Ad与2-Br（+）/ OTf（-）反应的产物是Ad = Ad：Br（+）-coll复合物，而4与2-Br（+）/ OTf的反应产物（-）为环状醚2-溴甲基四氢呋喃。与环己烯的反应更为复杂，涉及至少两个可逆形成的中间体，建议为coll-Br（+）和cyclohexene：Br（+）-coll，后者通过三氟甲磺酸酯的攻击而被捕获，得到反式-1-溴-2-三氟甲磺酰基环己烷。详细的动力学分析表明，可力丁，Ad = Ad，环己
• Neverov, Alexei A.; Feng, Helen Xiaomei; Hamilton, Kristen, Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3802 - 3810
  作者：Neverov, Alexei A.、Feng, Helen Xiaomei、Hamilton, Kristen、Brown

  DOI：——

  日期：——
• Br⁺ and I⁺ Transfer from the Halonium Ions of Adamantylideneadamantane to Acceptor Olefins. Halocyclization of 1,ω-Alkenols and Alkenoic Acids Proceeds via Reversibly Formed Intermediates
  作者：A. A. Neverov、R. S. Brown

  DOI：10.1021/jo951703f

  日期：1996.1.1

  The kinetics of the transfer of X(+) from the bromonium and iodonium ions of adamantylideneadamantane (1-Br+ and 1-I-) to some 1,omega-alkenols and alkenoic acids in ClCH2CH2Cl at 25 degrees C was investigated. In all cases, the expected products of halocyclization were observed. For the iodonium ion transfer the reaction kinetics are second order overall, first order in both 1-I+ and acceptor olefin. Transfer of the bromonium ion from 1-Br+ to these acceptor olefins exhibits different kinetic characteristics. In most cases, the rate of the Br+ transfer is subject to strong retardation in the presence of added parent olefin (Ad=Ad), suggestive of a common species rate depression. In some cases, such as 4-penten-1-ol (2b) and 4-pentenoic acid (4b), the reaction can be completely suppressed at high [Ad=Ad]. In other cases, such as 3-buten-1-ol (2a), 5-hexen-1-ol (2c), cyclohexene, 4-(hydroxymethyl)cyclohexene (3), and 5-endo-carboxynorbornene (5), added Ad=Ad does not suppress the reaction completely. In the cases of the 1,omega-alkenols, the reactions appear to exhibit kinetic terms that are greater than first order in alkenol. In these cases, alcohols such as l-pentanol also accelerate the reaction, pointing to the involvement of the hydroxyl group of the second alkenol as a catalytic species. A unifying mechanism consistent with the data that involves two reversibly formed intermediates is presented.
• Neverov, A.A.; Brown, R.S., Canadian Journal of Chemistry, 1994, vol. 72, # 12, p. 2540 - 2544
  作者：Neverov, A.A.、Brown, R.S.

  DOI：——

  日期：——
• Nagorski; Brown, Journal of the American Chemical Society, 1992, vol. 114, # 20, p. 7773 - 7779
  作者：Nagorski、Brown

  DOI：——

  日期：——