(2R,3S)-2-Methyl-5-phenyl-pentane-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S)-2-Methyl-5-phenyl-pentane-1,3-diol
• 英文别名: (2R,3S)-2-methyl-5-phenylpentane-1,3-diol
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: YEBNDAHPPGSPIV-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-Methyl-5-phenyl-pentane-1,3-diol 、 2,2-二甲氧基丙烷 在 CSA 作用下， 以 丙酮 为溶剂， 生成 (4S,5R)-2,2,5-trimethyl-4-phenethyl-1,3-dioxane
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via Allenylboronate Kinetic Resolution with (^dIpc)₂BH and Aldehyde Allylboration

  摘要：

  Enantioselective hydroboration of racemic allenylboronate (+/-)-1 with 0.48 equiv of ((d)Ipc)(2)BH at -25 degrees C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 degrees C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at -78 degrees C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87-94% ee.

  DOI：

  10.1021/ol3010968
• 作为产物：
  描述：

  (+/-)-(2R,3R)-2,5-dimethylhex-5-ene-1,3-diol 在 盐酸 、 重铬酸吡啶 、 zinc(II) tetrahydroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 (2R,3S)-2-Methyl-5-phenyl-pentane-1,3-diol
  参考文献：
  名称：

  Nakata, Tadashi; Tani, Yoichiro; Hatozaki, Masayoshi, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1411 - 1415

  摘要：

  DOI：

文献信息

• Efficient Organocatalytic Cross-Aldol Reaction between Aliphatic Aldehydes through Their Functional Differentiation
  作者：Taichi Kano、Hisashi Sugimoto、Keiji Maruoka

  DOI：10.1021/ja208873k

  日期：2011.11.16

  stereoselective asymmetric direct cross-aldol reaction between aliphatic aldehydes and α-chloroaldehydes has been developed as a method for the formation of the sole cross-aldol adduct with both enantio- and diastereocontrol, and either anti- or syn-aldol adducts were obtained in good to excellent stereoselectivities by use of proline or a novel axially chiral amino sulfonamide as catalyst.

  脂肪醛和 α-氯醛之间的化学和立体选择性不对称直接交叉羟醛反应已被开发作为形成具有对映和非对映控制的唯一交叉羟醛加合物的方法，以及反羟醛或顺羟醛加合物通过使用脯氨酸或新型轴向手性氨基磺酰胺作为催化剂，获得了良好的立体选择性。
• Regioselective Alkyl and Alkynyl Substitution Reactions of Epoxy Alcohols by the Use of Organoaluminum Ate Complexes:  Regiochemical Reversal of Nucleophilic Substitution Reactions
  作者：Minoru Sasaki、Keiji Tanino、Masaaki Miyashita

  DOI：10.1021/ol010062+

  日期：2001.5.1

  Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitution reactions by normal organoaluminum reagents, resulting in the formation of the C2-alkyl and C2-alkynyl substitution products in excellent yields.
• Nakata, Tadashi; Tani, Yoichiro; Hatozaki, Masayoshi, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1411 - 1415
  作者：Nakata, Tadashi、Tani, Yoichiro、Hatozaki, Masayoshi、Oishi, Takeshi

  DOI：——

  日期：——
• Diastereo- and Enantioselective Synthesis of (<i>E</i>)-2-Methyl-1,2-<i>syn</i>- and (<i>E</i>)-2-Methyl-1,2-<i>anti</i>-3-pentenediols via Allenylboronate Kinetic Resolution with (^<i>d</i>Ipc)₂BH and Aldehyde Allylboration
  作者：Jeng-Liang Han、Ming Chen、William R. Roush

  DOI：10.1021/ol3010968

  日期：2012.6.15

  Enantioselective hydroboration of racemic allenylboronate (+/-)-1 with 0.48 equiv of ((d)Ipc)(2)BH at -25 degrees C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 degrees C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at -78 degrees C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87-94% ee.