14-iodohexacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9>tetradecan-10-one | 112533-30-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 14-iodohexacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9>tetradecan-10-one
• 英文别名: 14-iodohexacyclo<6.6.0.0^2,6.0^3.13.0^4,11.0^5,9>tetradecan-10-one；14-iodohexacyclo<6.6.0^2,6.0^3,13.0^4,11.0^5,9>tetradecan-10-one；14-iodohexacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9]tetradecan-10-one；14-Iodohexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecan-10-one
• CAS: 112533-30-9；147976-42-9
• 化学式: C₁₄H₁₅IO
• 分子量: 326.177
• InChiKey: NLLGRONDIVJSRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  14-iodohexacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9>tetradecan-10-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以23 mg的产率得到14-hydroxyhexacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9>tetradecan-10-one
  参考文献：
  名称：

  Preparation of hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane-10,14-dione and derivatives

  摘要：

  DOI：

  10.1021/jo00240a036
• 作为产物：
  描述：

  七环[6.6.0.02,6.03,13.04,11.05,9.010,14]十四烷 在 lead(IV) acetate 、 sodium hydroxide 、 碘 、 三氟乙酸 、 lithium chloride 作用下， 以 苯 为溶剂， 反应 41.83h， 生成 14-iodohexacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9>tetradecan-10-one
  参考文献：
  名称：

  Preparation of hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane-10,14-dione and derivatives

  摘要：

  DOI：

  10.1021/jo00240a036

文献信息

• Reactions of phosphine with hexacyclo[6.6.0.02,6.03,13.04,11.05,9]-tetradecan-10-one derivatives
  作者：Tahsin J. Chow、Lih-Pyng Li、Vincent Y. R. Lee、Kuan-Jiuh Lin、Chong-Yow Chen

  DOI：10.1039/p29960002681

  日期：——

  reacts with triphenylphosphine or triethyl phosphite to form phosphonium salts 3 and 7 which fragment to an iodide 4 upon heating. The mechanism of C–C bond formation induced by phosphine and phosphite is discussed. A 1,3,2-dioxaphospholane 8 was synthesized from diketone 1 in two steps through an intermediate diol 10, although an attempt for a direct condensation of 1 and triphenylphosphine was unsuccessful

  碘酮2与三苯基膦或亚磷酸三乙酯反应形成phospho盐3和7，它们在加热时片段化成碘化物4。讨论了由膦和亚磷酸酯诱导的CC键形成机理。从二酮1分两步通过中间体二醇10合成了1,3,2-二氧杂磷杂环戊烷8，尽管尝试将1与三苯基膦直接缩合没有成功。通过半经验计算可以使反应合理化。报告了3和8的晶体衍射分析，并将其中一些键合参数与计算值进行了比较。
• Strained double bonds in two types of polycyclic hydrocarbons
  作者：Chin-Chuan Wei、Tahsin J. Chow、Ya-Ping Yang、Yao-Jung Chen

  DOI：10.1016/s0040-4020(01)80363-x

  日期：1993.3

  compounds 1 and 2 with pyramidalized double bond are prepared from their corresponding halides. Both of them are stable at ambient temperature but gradually transform to the epoxides upon exposing to air. Cycloaddition with either anthracene or cyclopentadiene yield the corresponding [4 + 2] adducts.

  由它们相应的卤化物制备具有金字塔状双键的两个多环化合物1和2。两者在环境温度下均稳定，但暴露于空气后逐渐转变成环氧化物。与蒽或环戊二烯进行环加成反应可生成相应的[4 + 2]加合物。
• Transannular Interactions in Polycyclic Hydrocarbons. The System of Cage-Shaped Hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane Derivatives
  作者：Tahsin J. Chow、Chin-Chuan Wei、Tung-Kung Wu、Hans-Dieter Martin、Bernhard Mayer

  DOI：10.1021/jo00122a055

  日期：1995.9

  The gas phase He(I alpha) photoelectron spectra (PES) of several ketone and olefinic derivatives of the titled compound are measured. The high energy pi-orbitals (HOMO and SHOMO) of 1e show an unusually large energy splitting of 0.90 eV, while the corresponding n-orbitals of 1d appear to be nearly degenerate (<0.1 eV). The difference between these observations is analyzed with the aid of theoretical models. It is concluded in this work that the pi-pi energy splitting of 1e is derived mainly from an orbital interaction transmitted through-space (TS) across the ring. Since such a nonbonded interaction is sensitive to distance, a conformational analysis of the cycloctane ring moiety of 1e is also performed. As compared to the result of PES, it seems that the ab initio (STO-3G) method is more reliable than AM1, in which the TS interaction is somewhat underestimated.
• CHOW, TAHSIN J.;WU, TUNG-KUNG, TETRAHEDRON LETT., 30,(1989) N0, C. 1279-1280
  作者：CHOW, TAHSIN J.、WU, TUNG-KUNG

  DOI：——

  日期：——
• CHOW, TAHSIN J.;WU, TUNG-KUNG, J. ORG. CHEM., 53,(1988) N 5, 1102-1103
  作者：CHOW, TAHSIN J.、WU, TUNG-KUNG

  DOI：——

  日期：——