(3S,4S)-(+)-3,4-isopropylidenedioxy-N,N,N',N'-tetramethyl-1,4-butanediamine | 63126-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-(+)-3,4-isopropylidenedioxy-N,N,N',N'-tetramethyl-1,4-butanediamine
• 英文别名: (4S,5S)-2,2-dimethyl-4,5-bis(dimethylaminomethyl)-1,3-dioxolane；(4S,5S)-4,5-bis(aminomethyl)-N⁴,N⁴,N⁵,N⁵-2,2-hexamethyl-1,3-dioxolane；(4S,5S)-N⁴,N⁴,N⁵,N⁵,2,2-hexamethyl-1,3-dioxolane-4,5-dimethaneamine；(+)-4S,5S-N(4),N(4),N(5),N(5),2,2-hexamethyl-1,3-dioxolane-4,5-dimethylamine；1,1'-((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(N,N-dimethylmethanamine)；1-[(4S,5S)-5-[(dimethylamino)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethylmethanamine
• CAS: 63126-30-7
• 化学式: C₁₁H₂₄N₂O₂
• 分子量: 216.324
• InChiKey: WOTDAPQUONJWPP-UWVGGRQHSA-N

物化性质

• 沸点：
  54 °C(Press: 0.8 Torr)
• 密度：
  0.9171 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯化苄 、 (3S,4S)-(+)-3,4-isopropylidenedioxy-N,N,N',N'-tetramethyl-1,4-butanediamine 以 氯仿 为溶剂， 反应 2.0h， 以8.1 g的产率得到(4S,5S)-(-)-N¹,N⁴-dibenzyl-2,3-dihydroxy-N¹,N¹,N⁴,N⁴-tetramethylbutane-1,4-diammonium dichloride
  参考文献：
  名称：

  Asymmetric transfer hydrogenation of carbonyl compounds catalyzed by rhodium nanoparticles

  摘要：

  Transfer hydrogenation of acetophenone and methyl benzoylformate with 2-propanol has been studied on rhodium nanoparticles obtained by the reduction of rhodium(I) complexes in the presence of optically active compounds, including chiral diamine S,S-DIODMA, (4S,5S)-N-4,N-4,N-5,N-5,2,2-hexamethyl-4,5-bis-(aminomethylene)-1,3-dioxolane, quaternary diammonium salt (4S,5S)-(-)-N-1,N-4-dibenzyl-2,3-dihydroxy-N-1,N-1,N-4,N-4-tetramethylbutane-1,4-diammonium dichloride, and (8S,9R)-(-)-cinchonidine. Increasing the modifier to Rh ratio leads to an increase in the enantiomeric excess (ee) of the reaction products. The greatest ee values (43.8% for (R)-1-phenylethanol and 58.2% for the methyl ester of (R)-mandelic acid) were achieved at (8S,9R)-(-)-cinchonidine/Rh ratios of 9:1 and 3:1, respectively. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2016.04.007
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 54.0h， 生成 (3S,4S)-(+)-3,4-isopropylidenedioxy-N,N,N',N'-tetramethyl-1,4-butanediamine
  参考文献：
  名称：

  DNA压缩中的立体异构体识别。

  摘要：

  DOI：

  10.1002/anie.200453774

文献信息

• Borohydride reduction of acetophenone and esters of dehydrocarboxylic acids in the presence of chiral cobalt(II) diamine complexes
  作者：L. O. Nindakova、B. A. Shainyan

  DOI：10.1007/s11172-005-0258-8

  日期：2005.2

  The catalytic reduction of acetophenone, methyl α-acetamidocinnamate, and dimethyl itaconate with alcohol-modified sodium borohydride was studied in the presence of complexes CoCl2·L2 (L2 are chiral C 2-symmetric diamines: (4S,5S)-2,2-dimethyl-4,5-bis(aminomethyl)-1,3-dioxolane, (4S, 5S)-2,2-dimethyl-4,5-bis(methylaminomethyl)-1,3-dioxolane, (4S, 5S)-2,2-dimethyl-4,5-bis(dimethylaminomethyl)-1,3-dioxolane, and (4S, 5S)-2,2-dimethyl-4,5-bis(diphenylaminomethyl)-1,3-dioxolane). The maximum enantiomeric excess of (S)-1-phenylethanol was 24%, that of dimethyl α-methylsuccinate was 38%.

  研究了在络合物 CoCl2-L2 （L2 为手性 C 2 对称二胺）存在下，用醇改性硼氢化钠催化还原苯乙酮、α-乙酰胺肉桂酸甲酯和衣康酸二甲酯的过程：(4S,5S)-2,2-dimethyl-4,5-bis(aminomethyl)-1,3-dioxolane, (4S, 5S)-2,2-dimethyl-4,5-bis(methylaminomethyl)-1,3-dioxolane, (4S、(4S，5S)-2,2-二甲基-4,5-双(二甲基氨基甲基)-1,3-二氧戊环，(4S，5S)-2,2-二甲基-4,5-双(二苯基氨基甲基)-1,3-二氧戊环)。(S)-1-苯基乙醇的最大对映体过量率为 24%，α-甲基琥珀酸二甲酯的最大对映体过量率为 38%。
• CoII and RhI complexes with C 2-symmetric chiral diamines of the dioxolane series
  作者：L. O. Nindakova、N. N. Chipanina、V. K. Turchaninov、M. V. Ustinov、B. A. Shainyan

  DOI：10.1007/s11172-006-0120-7

  日期：2005.10

  The reaction of di-μ-chlorobis(1,5-cyclooctadiene)dirhodium with (4S, 5S)-2,2-dimethyl-4,5-bis(methylaminomethyl)-1,3-dioxolane (1) gave the complex [Rh(cod)(1)]Cl (cod is 1,5-cyclooctadiene). The composition of the complexes CoCl2 · L2 and [Rh(cod)(L2)]X (L2 = 1, (4S,5S)-2,2-dimethyl-4,5-bis(aminomethyl)-1,3-dioxolane, and (4S, 5S)-2,2-dimethyl-4,5-bis(dimethylaminomethyl)-1,3-dioxolane; X = Cl, TfO) was studied using IR and 1H NMR spectroscopy. In the RhI cyclooctadienediamine complexes, the diene molecule forms a stronger bond with the metal atom than that in the cyclooctadienediphosphine analogs.

  二-μ-氯双(1,5-环辛二烯)二铑与(4S,5S)-2,2-二甲基-4,5-双(甲基氨基甲基)-1,3-二氧戊环(1)反应得到络合物[ Rh(cod)(1)]Cl（cod 是 1,5-环辛二烯）。络合物 CoCl2 · L2 和 [Rh(cod)(L2)]X (L2 = 1, (4S,5S)-2,2-二甲基-4,5-双(氨基甲基)-1,3-二氧戊环的组成，和(4S,5S)-2,2-二甲基-4,5-双(二甲氨基甲基)-1,3-二氧戊环；X = Cl, TfO)使用IR和1H NMR光谱进行了研究。在RhI环辛二烯二胺配合物中，二烯分子与金属原子形成的键比环辛二烯二膦类似物中的键更强。
• ——
  作者：L. O. Nindakova、B. A. Shainyan、A. I. Albanov

  DOI：10.1023/a:1014390314872

  日期：——

  Hydrogenation of alpha-acetamidocinnamic and itaconic acids and their esters was carried out in the presence of the cationic Rh-1 triflate complex with (+)-4S,5S-N-4,N-4,N-5,N-5,2,2-hexamethyl-1,3-dioxolane-4,5-dimethaneamine (DIODMA). The optical yields depended on the nature of the solvent and the hydrogen pressure and reached 30%. The catalytically active forms of the complexes and their transformations in the presence of phosphines, molecular hydrogen, and the substrate were studied by H-1 and P-31 NMR spectroscopy.
• SEEBACH D.; KALINOWSKI H.-O.; BASTANI B.; CRASS G.; DAUM H.; DOERR H.; DU+, HELV. CHIM. ACTA <HCAC-A4>, 1977, 60, NO 2, 301-325
  作者：SEEBACH D.、 KALINOWSKI H.-O.、 BASTANI B.、 CRASS G.、 DAUM H.、 DOERR H.、 DU+

  DOI：——

  日期：——
• Asymmetric transfer hydrogenation of carbonyl compounds catalyzed by rhodium nanoparticles
  作者：Lidiya O. Nindakova、Nataliya M. Badyrova、Vladimir V. Smirnov、Sergey S. Kolesnikov

  DOI：10.1016/j.molcata.2016.04.007

  日期：2016.8

  Abstract Transfer hydrogenation of acetophenone and methyl benzoylformate with 2-propanol has been studied on rhodium nanoparticles obtained by the reduction of rhodium(I) complexes in the presence of optically active compounds, including chiral diamine S , S -DIODMA, (4 S ,5 S )- N 4 , N 4 , N 5 , N 5 ,2,2-hexamethyl-4,5-bis-(aminomethylene)-1,3-dioxolane, quaternary diammonium salt (4 S ,5 S )-(-)-