螺[4.7]十二烷-12-酮 | 3002-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 螺[4.7]十二烷-12-酮
• 英文名称: Spiro<4,7>dodecan-6-on
• 英文别名: Spiro[4.7]dodecan-6-one；spiro[4.7]dodecan-12-one
• CAS: 3002-04-8
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: ZIBHAUBCYMTZOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  螺[4.7]十二烷-12-酮 在 lithium aluminium tetrahydride 作用下， 生成 Spiro<4.7>dodecan-6-ol
  参考文献：
  名称：

  Ionic reactions in the spiran series. III. Solvolysis of medium-sized-ring spiro compounds

  摘要：

  DOI：

  10.1021/jo01283a021
• 作为产物：
  描述：

  2-氧-1-环辛烷羧酸 在 sodium hydride 作用下， 生成 螺[4.7]十二烷-12-酮
  参考文献：
  名称：

  Ionic reactions in the spiran series. III. Solvolysis of medium-sized-ring spiro compounds

  摘要：

  DOI：

  10.1021/jo01283a021

文献信息

• Enantioselective Addition of Remote Alkyl Radicals to Double Bonds by Photocatalytic Proton-Coupled Electron Transfer (PCET) Deconstruction of Unstrained Cycloalkanols
  作者：Noelia Salaverri、Benedetta Carli、Sergio Díaz-Tendero、Leyre Marzo、José Alemán

  DOI：10.1021/acs.orglett.2c00662

  日期：2022.5.6

  ring opening of unstrained cycloalkanols by a proton-coupled electron transfer (PCET) process, to 2-acyl imidazoles previously coordinated to a rhodium-based chiral Lewis acid. High yields and enantioselectivites up to 99% are achieved in 1 h. Mechanistic investigations support the formation of the remote alkyl radical by a PCET process, and theoretical studies explain the observed stereochemistry

  在这里，我们报告了远程烷基自由基的对映选择性加成，该自由基是通过质子耦合电子转移 (PCET) 过程由未应变的环烷醇开环产生的，该自由基与先前与铑基手性路易斯酸配位的 2-酰基咪唑相配。在 1 小时内实现了高产率和高达 99% 的对映选择性。机理研究支持通过 PCET 过程形成远程烷基自由基，理论研究解释了在加成步骤中观察到的立体化学。
• The pinacol rearrangement of cyclopentylcycloheptane-1,1'-diol
  作者：R.D. Sands

  DOI：10.1016/0040-4020(65)80024-2

  日期：1965.1

  When cyclopentylcycloheptane-1,1'-diol was heated with dilute acid, the major product was spiro [5.6] dodecan-1-one. The diene, 1-(1-cyclopentenyl)cycloheptene, was a minor product, and no spiro [4.7] dodecan-6-one was found.

  当将环戊基环庚烷-1,1'-二醇与稀酸一起加热时，主要产物为螺[5.6]十二烷-1-酮。二烯1-（1-环戊烯基）环庚烯是次要产物，未发现螺[4.7]十二烷-6-一。
• Study of I-Strain Relief in the Intermediate When Forming Spiro Ketones from Unsymmetrical Cycloalkylidenecycloalkanes, Their Dibromides, and Their Pinacols
  作者：Richard D. Sands

  DOI：10.1021/jo00081a030

  日期：1994.1

  Three unsymmetrical intercyclic olefins, their dibromides, and their pinacols were prepared, each so the two carbons involved at the functional group were part of a different sized ring. The pinacols were reacted with 25% sulfuric acid and with boron trifluoride etherate, the dibromides with silver nitrate,and the olefins with mercuric acetate and with trifluoroperacetic acid. The predominant spiro ketone found in each product mixture was used to determine which carbon, and hence which size ring, could better undergo the sp(3) to sp(2) or the sp(2) to sp(3) transition. The findings were consistent with Brown's observations on ring strain.
• KAKIUCHI, KIYOMI;ITOGA, KAZUO;TSUGARU, TOSHINORI;HATO, YUKINORI;TOBE, YOS+, J. ORG. CHEM., 1984, 49, N 4, 659-665
  作者：KAKIUCHI, KIYOMI、ITOGA, KAZUO、TSUGARU, TOSHINORI、HATO, YUKINORI、TOBE, YOS+

  DOI：——

  日期：——