2,2-dimethyl-5-hydroxy-7-phenylheptan-3-one | 169271-04-9

• 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-dimethyl-5-hydroxy-7-phenylheptan-3-one
• 英文别名: 5-hydroxy-2,2-dimethyl-7-phenyl-3-heptanone；5-hydroxy-2,2-dimethyl-7-phenylheptan-3-one
• CAS: 169271-04-9
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: YHHMWCHYXRGIRS-UHFFFAOYSA-N

物化性质

• 沸点：
  385.1±30.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-dimethyl-5-hydroxy-7-phenylheptan-3-one 在 三乙基硅烷 、 4-甲基苯磺酸吡啶 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 生成 (E)-2,2-Dimethyl-7-phenyl-hept-4-en-3-one
  参考文献：
  名称：

  Highly Selective Reduction of Acyclic β-Alkoxy Ketones to Protected syn-1,3-Diols

  摘要：

  The conversion of 1-(2-methoxyethoxy)ethyl-protected beta-hydroxy ketones to syn-1,3-ethylidene acetals is effected by Et3SiH and SnCl4. This reaction is proposed to proceed via a cyclic oxocarbenium ion intermediate and provides the products in yields that range from 69 to 94% and with diastereoselectivities that are >200:1.

  DOI：

  10.1021/ol048801k
• 作为产物：
  描述：

  苯丙醛 、 allyl 4,4-dimethyl-3-oxopentanoate 在 ytterbium(III) chloride 、 tris(dibenzylideneacetone)dipalladium (0) 、 (+/-)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到2,2-dimethyl-5-hydroxy-7-phenylheptan-3-one
  参考文献：
  名称：

  异双金属催化烯丙基β-酮酯的脱羧醛醇反应

  摘要：

  涉及烯丙基β-酮酯的温和且选择性的杂双金属催化的脱羧醛醇反应已被开发。该反应在室温下由 Pd(0)-和 Yb(III)-DIOP 配合物促进，包括由烯丙基 β-酮酯原位形成酮烯醇化物，然后将烯醇化物加入醛。该反应是异双金属催化的一个新例子，其中优化的反应条件需要添加两种金属。

  DOI：

  10.1021/ja045981k

文献信息

• Diastereoselective Aldol and Reformatsky Reactions of<b><i>α</i></b>-Halo Carbonyl Compounds and Aldehydes Mediated by Titanium(II) Chloride
  作者：Akifumi Kagayama、Koji Igarashi、Isamu Shiina、Teruaki Mukaiyama

  DOI：10.1246/bcsj.73.2579

  日期：2000.11

  Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester with aliphatic aldehydes proceeded to afford β-hydroxy thioesters in good yields under mild conditions.

  通过在低温下在二氯甲烷-新戊腈中使用氯化钛 (II) 和碘化铜或碘化钠的组合，成功地进行了 α-溴酮与几种醛的高度非对映选择性羟醛反应。类似地，α-溴硫酯与脂肪醛的 Reformatsky 反应在温和条件下以良好的产率得到 β-羟基硫酯。
• Reformatsky-type reaction of α-haloketones promoted by titanium tetraiodide
  作者：Makoto Shimizu、Fumiko Kobayashi、Ryuuichirou Hayakawa

  DOI：10.1016/s0040-4020(01)00982-6

  日期：2001.11

  Titanium(IV) tetraiodide induces a Reformatsky-type reaction of α-iodoketones with carbonyl compounds to give β-hydroxy ketones in good to high yields.

  四碘化钛（IV）引发α-碘酮与羰基化合物的Reformatsky型反应，从而以良好或高收率得到β-羟基酮。
• Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes
  作者：Yoshihiro Inamoto、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1021/ol3001443

  日期：2012.2.17

  An indium triiodide catalyst promoted the direct transformation from esters to beta-hydroxycarbonyl compounds using hydrosilanes and silyl enolates by a one-stage process. Various esters were applicable, and the high chemoselectivity of this system brings compatibility to many functional groups: alkenyl, alkynyl, chloro, and hydroxy.
• NARASAKA, KOICHI;MIWA, TETSUO;HAYASHI, HIROKI;OHTA, MASAKO, CHEM. LETT., 1984, N 8, 1399-1402
  作者：NARASAKA, KOICHI、MIWA, TETSUO、HAYASHI, HIROKI、OHTA, MASAKO

  DOI：——

  日期：——
• Decarboxylative Aldol Reactions of Allyl β-Keto Esters via Heterobimetallic Catalysis
  作者：Sha Lou、John A. Westbrook、Scott E. Schaus

  DOI：10.1021/ja045981k

  日期：2004.9.1

  Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl beta-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl beta-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis

  涉及烯丙基β-酮酯的温和且选择性的杂双金属催化的脱羧醛醇反应已被开发。该反应在室温下由 Pd(0)-和 Yb(III)-DIOP 配合物促进，包括由烯丙基 β-酮酯原位形成酮烯醇化物，然后将烯醇化物加入醛。该反应是异双金属催化的一个新例子，其中优化的反应条件需要添加两种金属。