(3R)-3-phenyl-1,3-butanediol | 68330-54-1

• 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: (3R)-3-phenyl-1,3-butanediol
• 英文别名: (R)-3-phenyl-butane-1,3-diol；(R)-3-phenylbutane-1,3-diol；3-phenylbutane-1,3-diol；(-)-Phenyl-butandiol-(1,3)；(3R)-3-Phenylbutane-1,3-diol
• CAS: 68330-54-1
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: BQNJVHGCZBNKBG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4R,6R)-4,6-dimethyl-2-(2-hydroxy-2-phenylpropyl)-1,3-dioxane 在 盐酸 、 lithium aluminium tetrahydride 、 Amberlyst 15 作用下， 以 丙酮 为溶剂， 反应 10.5h， 生成 (3R)-3-phenyl-1,3-butanediol
  参考文献：
  名称：

  有机金属试剂与同手性 β-酮缩醛的不对称加成

  摘要：

  检查了有机锂试剂羰基加成到 β-酮缩醛的非对映选择性。将 MeLi 添加到衍生自 Pd(II) 催化的苯基乙烯基酮与 (R,R)-2,4-戊二醇的 β-酮缩醛中，得到 (4R,6R)-4,6-二甲基-2-[( 2R)-2-羟基-2-苯基丙基]-1,3-二恶烷在 75% de 中。

  DOI：

  10.1246/bcsj.61.3380

文献信息

• C−O Hydrogenolysis Catalyzed by Pd-PMHS Nanoparticles in the Company of Chloroarenes
  作者：Ronald J. Rahaim、Robert E. Maleczka

  DOI：10.1021/ol102757v

  日期：2011.2.18

  Catalytic Pd(OAc)2 and polymethylhydrosiloxane (PMHS), in conjunction with aqueous KF, and a catalytic amount of an aromatic chloride, effects the chemo-, regio-, and stereoselective deoxygenation of benzylic oxygenated substrates at room temperature in THF. Preliminary mechanistic experiments suggest the process to involve palladium−nanoparticle-catalyzed hydrosilylation followed by C−O reduction

  催化 Pd(OAc) 2和聚甲基氢硅氧烷 (PMHS) 与水性 KF 和催化量的芳族氯化物结合，在室温下在 THF 中影响苄基氧化底物的化学、区域和立体选择性脱氧。初步的机械实验表明该过程涉及钯-纳米颗粒催化的氢化硅烷化，然后是 CO 还原。氯芳烃添加剂似乎通过 HCl 的缓慢受控释放促进氢解过程。
• Copper(I)-Catalyzed Regioselective Asymmetric Addition of 1,4-Pentadiene to Ketones
  作者：Feng Zhong、Zhi-Zhou Pan、Si-Wei Zhou、Hai-Jun Zhang、Liang Yin

  DOI：10.1021/jacs.1c02084

  日期：2021.3.31

  E)/others ratio, which demonstrates the partial isomerization of (E)-allylcopper(I) species to (Z)-allylcopper(I) species through 1,3-migration. Subsequent Heck reaction and olefin metathesis compensate for the low efficiency with C1-1,4-dienes. The synthetic utility of the product is further demonstrated by a copper(I)-catalyzed regioselective borylation of the 1,3-diene group.

  通过使用市售的 1,4-戊二烯作为亲核试剂，实现了铜（I）催化的酮的区域选择性不对称烯丙基化。各种带有末端 ( Z )-1,3-二烯单元的手性叔醇以高 ( Z )/( E ) 比和高对映选择性生成。芳族酮和脂族酮均用作合适的底物。此外，与 ( E )-C 1 (烷基)-1,4-二烯的反应以中等产率进行，具有可接受的对映选择性，但 ( Z , E ) / 其他比率较低，这证明了 ( E )-烯丙基铜的部分异构化(I) 物种到 ( Z)-烯丙基铜 (I) 物种通过 1,3-迁移。随后的 Heck 反应和烯烃复分解用 C 1 -1,4-二烯弥补了低效率。该产品的合成效用通过铜 (I) 催化的 1,3-二烯基团的区域选择性硼酸化得到进一步证明。
• Resolution of Diols via Catalytic Asymmetric Acetalization
  作者：Ji Hye Kim、Ilija Čorić、Chiara Palumbo、Benjamin List

  DOI：10.1021/ja512481d

  日期：2015.2.11

  A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent

  使用手性限制的亚氨基二磷酸催化剂，通过不对称缩醛化实现了二醇的高度对映选择性动力学拆分。该反应对叔醇的拆分非常有效，选择性因子高达 >300。值得注意的是，即使在选择性因素仅为中等的情况下，高度对映体丰富的二醇也是通过立体发散拆分非对映缩醛获得的。
• Copper(I)-Catalyzed Enantioselective Addition of Enynes to Ketones
  作者：Xiao-Feng Wei、Xiao-Wei Xie、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/jacs.7b01254

  日期：2017.4.5

  A copper(I)-catalyzed enantioselective addition of enynes to ketones was developed. The method allows facile construction of enantiomerically enriched tertiary alcohols using skipped enynes as stable hydrocarbon pronucleophiles. The combination of a soft copper(I)-conjugated Brønsted base catalyst with a chiral diphosphine ligand, (S,S)-Ph-BPE, enabled chemoselective deprotonation of the skipped enynes

  开发了铜（I）催化的烯炔与酮的对映选择性加成。该方法允许使用跳过的烯炔作为稳定的烃亲核试剂轻松构建对映异构体富集的叔醇。软铜 (I)-共轭 Brønsted 碱催化剂与手性二膦配体 (S,S)-Ph-BPE 的组合，能够在带有本质上更具酸性的 α-质子的酮的存在下对跳过的烯炔进行化学选择性去质子化。催化生成的手性烯丙基铜物种对映-、非对映-、区域-和化学选择性与酮反应，从而表现出优异的底物通用性和官能团耐受性。亲核试剂的跳过的烯炔部分专门转化为顺式共轭烯炔，
• Enantioselective Small Molecule Synthesis by Carbon Dioxide Fixation using a Dual Brønsted Acid/Base Organocatalyst
  作者：Brandon A. Vara、Thomas J. Struble、Weiwei Wang、Mark C. Dobish、Jeffrey N. Johnston

  DOI：10.1021/jacs.5b04425

  日期：2015.6.17

  Carbon, dioxide exhibits many of the qualities of an ideal reagent: it is nontoxic, plentiful, and inexpensive. Unlike other gaseous reagents, however, it has found limited use in enantioselective synthesis. Moreover, unprecedented is a tool that merges one of the Simplest biological :approaches to catalysis-Bronsted acid/base activation with this abundant reagent. We describe a metal-free small molecule catalyst that achieves the three component reaction between a homoallylic alcohol, carbon dioxide, and an electrophilic Source of iodine. Cyclic carbonates are formed enantioselectively.