1-hydroxy-2,4,4-trimethyl-3-pentanone | 174358-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxy-2,4,4-trimethyl-3-pentanone
• 英文别名: 1-hydroxy-2,4,4-trimethylpentan-3-one
• CAS: 174358-63-5
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: SSKBRYOEAYVUGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1-hydroxy-2,4,4-trimethyl-3-pentanone 在 吡啶硼烷 、 四氯化钛 作用下， 生成 2,4,4-trimethylpentane-1,3-diol 、 rel-(2R,3S)-2,4,4-trimethyl-1,3-pentanediol
  参考文献：
  名称：

  BCl₃- and TiCl₄-Mediated Reductions of β-Hydroxy Ketones

  摘要：

  Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.

  DOI：

  10.1021/jo951549x
• 作为产物：
  描述：

  (Z)-(4,4-dimethylpent-2-en-3-yloxy)trimethylsilane 在 四氯化锡 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-hydroxy-2,4,4-trimethyl-3-pentanone
  参考文献：
  名称：

  Chiral SEM Ether−Tin Tetrachloride as an Enantioselective Hydroxymethylating Reagent for Silyl Enol Ethers:  γ-Effect of Silicon

  摘要：

  DOI：

  10.1021/ja9916613

文献信息

• Lewis Acid-Activated Chiral Leaving Group:  Enantioselective Electrophilic Addition to Prochiral Olefins
  作者：Hiroko Nakamura、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1021/jo020165l

  日期：2002.7.1

  A new strategy using a BINOL derivative as a chiral leaving group and Lewis acid has been developed for enantioselective alkylation of prochiral olefins. (R)-2,2'-Bis[2-(trimethylsilyl)ethoxymethyl]-1,1'-binaphthol is demonstrated to be an effective reagent for enantioselective hydroxymethylation of silyl enol ethers and trisubstituted alkenes. Electrophilic addition to prochiral olefins is accompanied

  已经开发了一种使用BINOL衍生物作为手性离去基团和路易斯酸的新策略，用于前手性烯烃的对映选择性烷基化。已证明（R）-2，2′-双[2-（三甲基甲硅烷基）乙氧基甲基] -1，1′-联苯酚是用于甲硅烷基烯醇醚和三取代烯烃的对映选择性羟甲基化的有效试剂。前手性烯烃的亲电加成伴随着乙缩醛的裂解，该缩醛被SnCl4双重激活，并且硅通过S（N）2取代过程产生了δ效应。使用该策略还描述了环状萜烯的对映选择性合成。
• TREPROSTINIL DERIVATIVES AND COMPOSITIONS AND USES THEREOF
  申请人：CORSAIR PHARMA, INC.

  公开号：US20180016222A1

  公开（公告）日：2018-01-18

  The present disclosure provides treprostinil derivatives that can act as prodrugs of treprostinil. The treprostinil derivatives can be used to treat any conditions responsive to treatment with treprostinil, including pulmonary hypertension, such as pulmonary arterial hypertension.
• US9394227B1
  申请人：——

  公开号：US9394227B1

  公开（公告）日：2016-07-19
• [EN] PROCESS FOR THE PREPARATION OF 2,2,4,4-TETRAALKYLCYCLOBUTANE-1,3-DIOLS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE 2,2,4,4-TÉTRAALKYLCYCLOBUTANE-1,3-DIOLS
  申请人：EASTMAN CHEM CO

  公开号：WO2012078384A1

  公开（公告）日：2012-06-14

  Disclosed is a process for the preparation of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of the corresponding 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the vapor phase in the presence of a supported catalyst. The process is useful for the preparation of 2,2,4,4-tetramethylcyclobutane-1,3-diol from 2,2,4,4-tetramethylcyclobutane-1,3-dione. The process can produce a 2,2,4,4-tetraalkylcyclobutane-1,3-diol product having a cis:trans isomer ratio of 1:1 or greater.
• BCl₃- and TiCl₄-Mediated Reductions of β-Hydroxy Ketones
  作者：Christopher R. Sarko、Scott E. Collibee、Allison L. Knorr、Marcello DiMare

  DOI：10.1021/jo951549x

  日期：1996.1.1

  Syn-selective reduction protocols for beta-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively, Reductions are conducted at -78 degrees C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents, Added acid-scavenging agents are detrimental to reaction selectivity, An A((1,3))-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.