9,9-Dimethyl-10-methylen-9,10-dihydrophenanthren | 16004-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,9-Dimethyl-10-methylen-9,10-dihydrophenanthren
• 英文别名: 9,9-Dimethyl-10-methylen-phenanthren；9,9-Dimethyl-10-methylene-9,10-dihydrophenanthrene；9,9-dimethyl-10-methylidenephenanthrene
• CAS: 16004-52-7
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: UHYPMPRIWXGXFW-UHFFFAOYSA-N

物化性质

• 熔点：
  31.0-31.5 °C
• 沸点：
  140-141 °C(Press: 1.5 Torr)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9,9-Dimethyl-10-methylen-9,10-dihydrophenanthren 、 氯 生成 9-(Chloromethyl)-9,10-dimethylphenanthren-10-ylium
  参考文献：
  名称：

  LOKTEV V. F.; KORCHAGINA D. V.; SHUBIN V. G., IZV. SIB. OTD. AN CCCP CEP. XIM. N., 1980, HO 14/6, 86-96

  摘要：

  DOI：
• 作为产物：
  描述：

  9-甲基芴 在 甲酸 作用下， 反应 16.0h， 生成 9,9-Dimethyl-10-methylen-9,10-dihydrophenanthren
  参考文献：
  名称：

  Studies in Stereochemistry. XXXIII. Approaches to Models for 1,3-Asymmetric Induction

  摘要：

  DOI：

  10.1021/ja00892a009

文献信息

• Palladium-Catalyzed Controlled Carbopalladation of Benzyne
  作者：Eiji Yoshikawa、K. V. Radhakrishnan、Yoshinori Yamamoto

  DOI：10.1021/ja001205a

  日期：2000.8.1

  derivatives 16 in moderate yields (ii). The reaction of benzyne precursor 1a with the alkynes 15a−c,f−h in the presence of Pd(OAc)2 (5 mol %)−(o-tolyl)3P (5 mol %) catalyst and CsF (2.0 equiv) in CH3CN gave the phenanthrene derivatives 17 (iii), whereas the reaction of 1a with the alkynes 15a,b,i in the presence of the same catalysts and CsF in CH3CN−toluene gave the indene derivatives 18 in good yields (iv)

  2-三甲基甲硅烷基苯基三氟甲磺酸盐 1a，一种苄基前体，在 CsF（2.0 当量）和 Pd2(dba)3·CHCl3 (2.5 mol %)-dppf (5 mol %) 存在下与烯丙基氯化物 2a-f 反应:1 CH3CN 和 THF 的混合溶剂以良好的产率 (i) 产生菲衍生物 3 及其次要的区域异构体 4，并且 1a 与 2a 和内部炔烃 15a,ce 的反应以中等产率提供萘衍生物 16 （二）。在 Pd(OAc)2 (5 mol %)-(o-tolyl)3P (5 mol %) 催化剂和 CsF (2.0 equiv) 存在下，苄基前体 1a 与炔烃 15a-c,f-h 的反应CH3CN 得到菲衍生物 17 (iii)，而 1a 与炔烃 15a,b,i 在相同催化剂和 CsF 存在下在 CH3CN-甲苯中的反应以良好的产率 (iv) 得到茚衍生物 18。
• Nickel-catalyzed highly chemoselective cocyclotrimerization of arynes with allenes: a novel method for 10-methylene-9,10-dihydrophenanthrenesElectronic supplementary information (ESI) available: synthesis and characterization data of compounds 3. See http://www.rsc.org/suppdata/cc/b3/b315795d/
  作者：Jen-Chieh Hsieh、Dinesh Kumar Rayabarapu、Chien-Hong Cheng

  DOI：10.1039/b315795d

  日期：——

  The NiBr2(dppe)–Zn system effectively catalyzes the [2+2+2] cocyclotrimerization of arynes with allenes, leading to 10-methylene-9,10-dihydrophenanthrenes in moderate to good yields. The cocyclotrimerization is highly selective with only the internal double bond of the allenes being involved in the reaction.

  NiBr2(dppe)–Zn体系能有效地催化芳炔与丙二烯的[2+2+2]协同三聚环化反应，生成中等至较好产率的10-甲烯基-9,10-二氢菲。该协同三聚环化反应具有高度选择性，仅涉及丙二烯的内部双键参与反应。
• Pd(II)-NHDC-Functionalized UiO-67 Type MOF for Catalyzing Heck Cross-Coupling and Intermolecular Benzyne–Benzyne–Alkene Insertion Reactions
  作者：Yong-Liang Wei、Yue Li、Yun-Qi Chen、Ying Dong、Jia-Jia Yao、Xin-Yue Han、Yu-Bin Dong

  DOI：10.1021/acs.inorgchem.7b03271

  日期：2018.4.16

  an Pd-NHDC-containing UiO-67 type MOF (UiO-67-Pd-NHDC) was prepared on the basis of a size-matched ligand mixture of biphenyl-4,4′-dicarboxylic acid/Pd-NHDC-H2L (9/1) and ZrCl4 under solvothermal conditions. The obtained UiO-67-Pd-NHC MOF can be a highly heterogeneous catalyst to promote Heck cross-coupling and intermolecular benzyne–benzyne–alkene insertion reactions.

  成功合成了新型的钯N-杂环双卡宾二羧酸钯配体（Pd-NHDC-H 2 L）。此外，基于联苯-4,4'-二羧酸/ Pd-NHDC-的大小匹配的配体混合物，制备了含Pd-NHDC的UiO-67型MOF（UiO-67- Pd-NHDC）在溶剂热条件下为H 2 L（9/1）和ZrCl 4。获得的UiO-67-Pd-NHC MOF可能是高度异质的催化剂，可促进Heck交叉偶联和分子间苯并-苯并-烯烃插入反应。
• Palladium-Catalyzed Intermolecular Controlled Insertion of Benzyne-Benzyne-Alkene and Benzyne-Alkyne-Alkene—Synthesis of Phenanthrene and Naphthalene Derivatives
  作者：Eiji Yoshikawa、Yoshinori Yamamoto

  DOI：10.1002/(sici)1521-3773(20000103)39:1<173::aid-anie173>3.0.co;2-f

  日期：2000.1.3

  Aryne reagents, unlike alkynes, undergo insertion by allyl palladium complexes. The verification of the conversion described here is shown using Equation (1) as an example. The reaction proceeds in a few hours in refluxing acetonitrile to give the phenanthrene derivative in up to 71 % yield.
• <b>Studies in Stereochemistry. XXXIII. Approaches to Models for 1,3-Asymmetric Induction</b>
  作者：Donald J. Cram、Donald R. Wilson

  DOI：10.1021/ja00892a009

  日期：1963.5