1-chloro-2-adamantanone | 81315-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-chloro-2-adamantanone
• 英文别名: Chloro-adamantanone；1-chloroadamantan-2-one
• CAS: 81315-72-2
• 化学式: C₁₀H₁₃ClO
• 分子量: 184.666
• InChiKey: VPBFZQBGVOQBIV-UHFFFAOYSA-N

物化性质

• 沸点：
  287.0±13.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  1-chloro-2-adamantanone 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 1-chloro-2-adamantanone tosylhydrazone sodium salt
  参考文献：
  名称：

  Substituent effects on the regioselectivity of intramolecular carbene carbon-hydrogen insertion. Cyclizations of 1- and 5-substituted 2-adamantylidenes

  摘要：

  DOI：

  10.1021/jo00134a005
• 作为产物：
  描述：

  4-protoadamantanone 在 lithium aluminium tetrahydride 、 jones reagent 、 五氯化磷 、 硫酸 作用下， 以 四氯化碳 、 乙醚 、 丙酮 为溶剂， 反应 17.03h， 生成 1-chloro-2-adamantanone
  参考文献：
  名称：

  Substituent effects on the regioselectivity of intramolecular carbene carbon-hydrogen insertion. Cyclizations of 1- and 5-substituted 2-adamantylidenes

  摘要：

  DOI：

  10.1021/jo00134a005

文献信息

• Dioxetane radical cations in solution. An ESR and cyclic voltammetry study
  作者：Stephen F. Nelsen、Daniel L. Kapp、Fabian. Gerson、Javier. Lopez

  DOI：10.1021/ja00265a030

  日期：1986.3

  L'oxydation electrochimique du diadamantylidene-2,2' conduit au radical cation du spiro [adamantane-2:3'-dioxetanne-1',2'-4':2''-adamantane]. Spectres RPE de ce radical

  L'oxydationelectrochimique du diadamantylidene-2,2' 导管 au 自由基阳离子 du spiro [adamantane-2:3'-dioxetanne-1',2'-4':2''-adamantane]。Spectres RPE de ce激进
• 1, 2 chemiluminescent dioxetanes of improved performance
  申请人：Tropix, Inc.

  公开号：US05847161A1

  公开（公告）日：1998-12-08

  A new class of stable dioxetanes bears a polycyclic stabilizing group and aryloxy moiety, the oxygen atom of which is provided with a protective group which can be removed by an enzymatic or chemical trigger admixed with the dioxetane. The polycyclic stabilizing group is preferably spiroadamantane. The group further bears an alkoxy, aryloxy, aralkyloxy or cycloalkyloxy moiety which is partially or completely substituted with halogens, particularly fluorine and chlorine. Proper selection of electron active groups on the stabilizing moiety, the aryl group and the OR group yields enhanced enzyme kinetics, superior light intensity and excellent detection sensitivity in various assays.

  一种新型稳定的二氧杂环烷类化合物，其具有多环稳定基团和芳氧基团，其中氧原子带有保护基团，该保护基团可以通过酶或化学触发剂与二氧杂环烷混合后去除。多环稳定基团优选为螺环戊烷基团。该基团进一步带有烷氧基团、芳氧基团、芳基烷氧基团或环烷氧基团，部分或完全被卤素，特别是氟和氯取代。在稳定基团、芳基和OR基团上适当选择电子活性基团，可在各种检测中提高酶动力学、光强度和检测灵敏度。
• Solvolyses of Bicyclo[2.2.2]oct-1-yl and 1-Adamantyl Systems Containing an Ethylidene Substituent on the 2-Position: Typical Examples of Rate Enhancements Ascribed to Relief of F-Strain
  作者：Yasushi Ohga、Motohiro Munakata、Toshikazu Kitagawa、Tomomi Kinoshita、Ken'ichi Takeuchi、Yasuo Oishi、Hiroshi Fujimoto

  DOI：10.1021/jo00094a012

  日期：1994.7

  The first typical examples are described on the solvolysis rate enhancements ascribed to the relief of F-strain between an alkyl group and the leaving group atom directly attached to the reaction center. The rates and products of solvolyses in ethanol were studied for 2-methylene- and (Z)- and (E)-2-ethylidenebicyclo[2.2.2]oct-1-yl triflates. Solvolyses were also conducted in ethanol and 2,2,2-trifluoroethanol (TFE) on 2-methylene- and (Z)- and (E)-2-ethylidene-1-adamantyl compounds having OMs, F, Cl, Br, or I asa leaving group. Ah the substrates gave the corresponding bridgehead substitution products as kinetic control products. The Z:E rate ratios at 25 degrees C were 217 +/- 6 for 2-ethylidenebicyclo[2.2.2]oct-1-yl triflates (ethanol) and 109 +/- Il(ethanol) and 117 fl(TFE)for 2-ethylidene-1-adamantyl mesylates. O-18 scrambling studies on the ethanolyses of(Z)- and (E)2-ethylidene-1-adamantyl mesylates showed that the titrimetrically determined Z:E rate ratios can be used as a measure of the rate ratios for the ionization step. The Z:E rate ratio in TFE at 25 degrees C for 2-ethylidene-1-adamantyl halides varied in the sequence F (ca. 70), Cl(1020 +/- 160), Br (2230 +/- 90), and I (9500 +/- 280). The significant increases in the rate ratio with the increase in the atomic size of halogen were explained in terms of the presence of F-strain in the Z substrates and its essential absence in the E substrates. Linear correlations were found in a plot of 1.36 x log[k(Z)/k(E)] against the MM2 steric energy difference between the Z and E isomers (slope 1.0) and against Hansch's Es, demonstrating the significance of F-strain effect in the enhanced rates of the (Z)-2-ethylidene-1-adamantyl system. These correlations showed an intercept of 0.8 kcal mol(-1), which suggested the greater stability of the (Z)-2-ethylidene-1-adamantyl cation than the corresponding E cation by this amount. Ab initio calculations (RHF/G-31G**) showed that the Z cation is more stable than the E cation by 1.0 kcal mol(-1), and that the large Z:E rate ratios are in part ascribed to the difference in the cation stability.
• HIRSL-STARCEVIC, S.;MAJERSKI, Z., J. ORG. CHEM., 1982, 47, N 13, 2520-2525
  作者：HIRSL-STARCEVIC, S.、MAJERSKI, Z.

  DOI：——

  日期：——
• CHEMILUMINESCENT 3-(SUBSTITUTED ADAMANT-2'-YLIDENE) 1,2-DIOXETANES
  申请人：TROPIX, INC.

  公开号：EP0497972A1

  公开（公告）日：1992-08-12