2-<2-<2-(Hydroxymethyl)phenyl>ethynyl>benzaldehyde | 18887-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<2-<2-(Hydroxymethyl)phenyl>ethynyl>benzaldehyde
• 英文别名: 2-((2-(hydroxymethyl)phenyl)ethynyl)benzaldehyde；2-Formyl-2'-hydroxymethyl-diphenylacetylen；2-[2-[2-(Hydroxymethyl)phenyl]ethynyl]benzaldehyde
• CAS: 18887-53-1
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: JIZYZEVDDMJRDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<2-<2-(Hydroxymethyl)phenyl>ethynyl>benzaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 2-[2-(2-羟甲基苯基)-1-乙炔基]苯基甲醇
  参考文献：
  名称：

  Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

  摘要：

  一种高效的无过渡金属合成二氢异苯并呋喃衍生物的方法已被开发，该方法通过介导铯碳酸盐对芳香族炔醇进行分子内氢烷氧化反应。反应以区位选择性进行，专一生成5-exo-dig产物，并且仅观察到新生成双键的Z-异构体。该新方法具有反应条件温和、操作便捷和选择性满意的特点。

  DOI：

  10.1007/s11696-020-01159-5
• 作为产物：
  描述：

  2,2'-(ethyne-1,2-diyl)dibenzaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 2-<2-<2-(Hydroxymethyl)phenyl>ethynyl>benzaldehyde
  参考文献：
  名称：

  Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

  摘要：

  一种高效的无过渡金属合成二氢异苯并呋喃衍生物的方法已被开发，该方法通过介导铯碳酸盐对芳香族炔醇进行分子内氢烷氧化反应。反应以区位选择性进行，专一生成5-exo-dig产物，并且仅观察到新生成双键的Z-异构体。该新方法具有反应条件温和、操作便捷和选择性满意的特点。

  DOI：

  10.1007/s11696-020-01159-5

文献信息

• Gold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of<i>ortho</i>-(Alkynyl)styrenes
  作者：Ana M. Sanjuán、Muhammad A. Rashid、Patricia García-García、Alberto Martínez-Cuezva、Manuel A. Fernández-Rodríguez、Félix Rodríguez、Roberto Sanz

  DOI：10.1002/chem.201405789

  日期：2015.2.9

  Indenes and related polycyclic structures have been efficiently synthesized by gold(I)‐catalyzed cycloisomerizations of appropriate ortho‐(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5‐endo‐dig cyclization. Interestingly, a complete switch in the selectivity of the cyclization of o‐(alkynyl)‐α‐methylstyrenes

  吲哚和相关的多环结构已通过金（I）催化的适当邻-（炔基）苯乙烯的环异构化反应有效地合成。在二取代烯烃的末端位置被证明是必要的，以获得从一个正式的5个产品始发-内-挖环化。有趣的是，通过向反应介质中添加醇，可以观察到邻-（炔基）-α-甲基苯乙烯从6-内酯到5-内酯的环化选择性的完全变化。这样就可以合成在C1处有一个全碳四元中心的有趣的茚满。此外，二氢苯并[ a]芴可通过串联环异构化/ 1,2-氢化物迁移过程从在苯乙烯部分的β-位带有仲烷基的底物获得。此外，通过分子内金催化结构中带有亲核试剂的邻-（炔基）苯乙烯的烷氧基环化反应，获得了多种多环化合物。最后，使用手性金配合物可以以良好的对映选择性获得难以捉摸的手性1 H-茚。
• all-Z-Tribenzo[12]-, tetrabenzo[16]- and pentabenzo[20]annulenes
  作者：Yoshiyuki Kuwatani、Tadahiro Yoshida、Ayako Kusaka、Masahiko Iyoda

  DOI：10.1016/s0040-4039(99)02062-6

  日期：2000.1

  A new synthetic strategy of all-Z-[n]benzo[4n]annulenes, which is based on the intramolecular pinacol coupling, followed by the Corey–Winter procedure, has been developed, and three annulenes have been successfully synthesized using this strategy.

  的一种新的合成策略所有- ž - [ Ñ ]苯并[4 Ñ ]轮烯，它是基于分子内频哪醇偶联，然后由科里-冬季过程，已经开发和三个轮烯已使用这种策略成功地合成。
• An Unusual Example of a 6-Endo-Dig Addition to an Unactivated Carbon-Carbon Triple Bond
  作者：Albert Padwa、Keith E. Krumpe、M. David Weingarten

  DOI：10.1021/jo00122a047

  日期：1995.9

  Methyl 2-[2-[2-(1-hydroxy-1-ethyl)phenyl]ethynyl]benzoate was prepared as an intermediate for subsequent conversion to an a-diazo ketone. Under the basic conditions used to hydrolyze the methyl ester, the neighboring hydroxyl functionality underwent reaction with the unactivated acetylenic group, producing a benzopyranyl-substituted alpha-diazoacetophenone. Treatment of this diazocarbonyl compound with a catalytic quantity of rhodium(II) mandelate afforded a novel dibenzo[a,e]cyclononenone derivative. The reaction proceeds via an initially formed oxonium ylide which rearranges further by means of a 1,2-alkyl shift. A prime factor in determining the direction of internal cyclization to the triple bond is the presence of the carbomethoxy group in the ortho position of the beta-phenyl ring. Thus, in contrast with related systems which exhibit a clear preference for 5-exo-dig cyclization at the acetylenic center, the 6-endo-dig addition is the preferred pathway for the o-formyl- and o-carbomethoxy-substituted alkynyl alcohols. Careful monitoring of the reaction actually showed that the reaction proceeds by initial formation of the 5-exo-dig product followed by a novel rearrangement to the 6-endo product.
• Intramolecular Addition to an Unactivated Carbon-Carbon Triple Bond via an Apparent 6-Endo Digonal Pathway
  作者：M Weingarten

  DOI：10.1016/00404-0399(50)0891f-

  日期：1995.7.3
• Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions
  作者：Shu-Yan Yu、Li-Hong Gao、Jing-Xin Wu、Hong-Bing Lan、Yi Ma、Zhi-Gang Yin

  DOI：10.1007/s11696-020-01159-5

  日期：2020.10

  An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

  一种高效的无过渡金属合成二氢异苯并呋喃衍生物的方法已被开发，该方法通过介导铯碳酸盐对芳香族炔醇进行分子内氢烷氧化反应。反应以区位选择性进行，专一生成5-exo-dig产物，并且仅观察到新生成双键的Z-异构体。该新方法具有反应条件温和、操作便捷和选择性满意的特点。