2-thiocyanocycloheptanone | 27008-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-thiocyanocycloheptanone
• 英文别名: 2-thiocyanatocycloheptanone；2-oxocycloheptyl thiocyanate；2-thiocyanatocycloheptan-1-one；2-Thiocyanatocycloheptanon；(2-Oxocycloheptyl) thiocyanate
• CAS: 27008-21-5
• 化学式: C₈H₁₁NOS
• 分子量: 169.247
• InChiKey: KGJPENLGDXAQRD-UHFFFAOYSA-N

物化性质

• 沸点：
  110-111 °C(Press: 1.5 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thiocyanocycloheptanone 在 硫代乙酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以76%的产率得到3,4,5,6,7,8-hexahydrocycloheptathiazole-2-thione
  参考文献：
  名称：

  Ali, S. Mahmoud; Clarke, David; Cliff, Geoffrey R., Journal of Chemical Research, Miniprint, 1990, # 11, p. 2638 - 2655

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-Dimethoxy-2-thiocyanato-cycloheptane 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 2-thiocyanocycloheptanone
  参考文献：
  名称：

  Ali, S. Mahmoud; Clarke, David; Cliff, Geoffrey R., Journal of Chemical Research, Miniprint, 1981, # 8, p. 2901 - 2927

  摘要：

  DOI：

文献信息

• Iron(III) Chloride as Mild and Efficient Reagent for the α-Thiocyanation of Ketones: An Expedient Synthesis of α-Oxo Thiocyanates
  作者：Jhillu Yadav、Basi Reddy、Ummareddy Reddy、Darshanoju Chary

  DOI：10.1055/s-2008-1072517

  日期：2008.4

  A simple and efficient method for the α-thiocyanation of ketones has been developed; anhydrous iron(III) chloride is used under mild conditions to produce α-oxo thiocyanates in good to high yields and with high selectivity. The use of inexpensive and readily available iron(III) chloride makes this procedure simple, convenient, and practical.

  我们开发了一种简单有效的方法来进行酮类化合物的δ-硫氰酸化反应；在温和的条件下使用无水氯化铁（III），可生成δ-氧代硫氰酸盐，收率高且选择性好。使用廉价易得的氯化铁（III）使这一过程简单、方便、实用。
• α-Selective C(sp³)–H Thio/Selenocyanation of Ketones with Elemental Chalcogen
  作者：Jin-Cheng Li、Wen-Xia Gao、Miao-Chang Liu、Yun-Bing Zhou、Hua-Yue Wu

  DOI：10.1021/acs.joc.1c02431

  日期：2021.12.3
• NBS or DEAD as effective reagents in α-thiocyanation of enolizable ketones with ammonium thiocyanate
  作者：B.V. Subba Reddy、S. Madhu Sudana Reddy、Ch. Madan

  DOI：10.1016/j.tetlet.2011.01.035

  日期：2011.3

  Ketones possessing a-hydrogen undergo smooth thiocyanation with ammonium thiocyanate in the presence of N-bromosuccinimide (NBS) at room temperature in acetonitrile under neutral conditions to produce the corresponding alpha-ketothiocyanates in excellent yields with high selectivity. The use of NBS makes this procedure simple, convenient and cost effective. In addition, diethyl azodicarboxylate (DEAD) was also found to promote this reaction under mild conditions. (c) 2011 Elsevier Ltd. All rights reserved.
• Iodine/MeOH as a novel and versatile reagent system for the synthesis of α-ketothiocyanates
  作者：J.S. Yadav、B.V. Subba Reddy、U.V. Subba Reddy、A.D. Krishna

  DOI：10.1016/j.tetlet.2007.05.143

  日期：2007.7

  Ketones possessing alpha-hydrogens undergo smooth thiocyanation with ammonium thiocyanate in the presence of molecular iodine in refluxing methanol to produce the corresponding alpha-ketothiocyanates in excellent yields with high selectivity. The use of iodine makes this procedure simple, convenient and cost effective. (c) 2007 Published by Elsevier Ltd.
• ALI, S. MAHMOUD;CLARKE, DAVID;CLIFF, GEOFFREY R.;MORRISON, GEORGE A.
  作者：ALI, S. MAHMOUD、CLARKE, DAVID、CLIFF, GEOFFREY R.、MORRISON, GEORGE A.

  DOI：——

  日期：——