(2R,4R)-pentane-2,4-diamine | 34998-98-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,4R)-pentane-2,4-diamine
• 英文别名: (R,R)-2,4-pentanediamine；(2R,4R)-diaminopentane
• CAS: 34998-98-6
• 化学式: C₅H₁₄N₂
• 分子量: 102.18
• InChiKey: JGQDLMSXMOGEMC-RFZPGFLSSA-N

物化性质

• 沸点：
  146.4±8.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R)-pentane-2,4-diamine 在 ammonium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-Amino-N-[(1R,3R)-3-(2-amino-acetylamino)-1-methyl-butyl]-acetamide
  参考文献：
  名称：

  含有六元螯合环的金属配合物。四、2,4-戊二胺衍生的四胺二氯钴(III)配合物的制备及结构

  摘要：

  四胺配体, 4,6-二甲基-3,7-二氮杂-1,9-壬二胺 (2,3", 2-tet), 6,8-二甲基-2,5,9,12-四氮杂十三烷 (N, N'-Me2-2,3", 2-tet) 和 4,9-二甲基-5,8-二氮杂-2,11-十二烷二胺 (3",2,3"-tet) 使用 RR 制备- 和 RS-2,4-戊二胺作为起始原料。制备并表征了六种具有这些配体的反式二氯钴 (III) 配合物。在这些配合物中，获得了三种光学活性配合物。根据分子模型、PMR、吸收光谱和CD光谱，这些配合物中的RR-2,4-戊二胺和RS-2,4-戊二胺部分被认为分别具有λ-skew-boat和椅子构象.

  DOI：

  10.1246/bcsj.48.1205
• 作为产物：
  描述：

  2,4-戊硫醇二氧(杂)芑 在 sodium hydroxide 、 镍 作用下， 生成 (2R,4R)-pentane-2,4-diamine
  参考文献：
  名称：

  Regional rule for the optical activity of conformational isomers of octahedral transition metal complexes

  摘要：

  DOI：

  10.1021/ja00765a028

文献信息

• Synthesis of New Chiral Derivatives of N,N′-Dimethylpropyleneurea (DMPU) and Examination of Their Influence on the Regio- and Enantioselectivity of Addition of 2-(1,3-Dithianyl)lithium to Cyclohex-2-en-1-one
  作者：Eusebio Juaristi、Marcos Hernández-Rodríguez、Heraclio López-Ruiz、Judit Aviña、Omar Muñoz-Muñiz、Michiya Hayakawa、Dieter Seebach

  DOI：10.1002/1522-2675(200207)85:7<1999::aid-hlca1999>3.0.co;2-k

  日期：2002.7

  another type of derivative is substituted at C(4) and C(6) of the heterocyclic ring (7). The potential of these chiral Lewis bases as promoters in the regio- and/or enantioselective addition of 2-(1,3-dithianyl)lithium to cyclohex-2-en-1-one was explored; they are all unable to effect enantioselective addition; the derivatives with branched substituents at the N-atoms do not shift the addition mode from

  描述了三种新的 DMPU 手性衍生物（N,N'-二甲基丙烯脲）的制备（方案 2-4）；一种衍生物在四氢嘧啶-2(1H)-一个环 (2 和 4) 的 N 原子上带有 1-苯乙基或 1-环己基乙基，另一种衍生物在 C(4) 和 C(6) 处被取代) 的杂环 (7)。探索了这些手性路易斯碱在 2-(1,3-二噻吩基)锂与 cyclohex-2-en-1-one 的区域选择性和/或对映选择性加成中作为促进剂的潜力；它们都不能实现对映选择性加成；在 N 原子上具有支化取代基的衍生物不会将加成模式从 1,2 转变为 1,4，而 3,4,5,6-tetrahydro-1,3,4,6-tetramethylpyrimidin-2(1H )-一个可以（方案 5）。结果提供了有关亲核有机锂试剂性质的有用信息：显然，N 原子上的支链取代基对四氢嘧啶-2(1H)-one 的 CO O 原子上的 Li 络合的空间位阻（参见图中
• Efficient stereochemical regulation of octahedral cobalt(<scp>III</scp>) complexes by a chiral bidentate ligand. Part 2. Remarkable effect of the chelate-ring size in the stereoselective formation of sym-cis-(ethylenediamine-N,N′-diacetato)(pentane-2,4-diamine)cobalt(<scp>III</scp>)
  作者：Morio Yashiro、Takashi Murata、Mitsunobu Sato、Masao Kosaka、Kimiko Kobayashi、Tosio Sakurai、Sadao Yoshikawa、Makoto Komiyama、Shigenobu Yano

  DOI：10.1039/dt9940001511

  日期：——

  The chiral diamine (2R), (4R)-pentane-2,4-diamine (2R,4R-ptn) has been found efficiently to regulate the stereochemistry of the cobalt(III) complex [Co(edda)(2R,4R-ptn)]+(edda = ethylenediamine-N,N′-diacetate). The product ratio Λ-sym-cis:Δ-sym-cis is 3:97. The stereoselectivity is surprisingly high in comparison with that for the analogous complex involving (1R),(2R)-cyclohexane-1,2-diamine (R,R-chxn)

  已发现手性二胺（2 R），（4 R）-戊烷-2,4-二胺（2 R，4 R -ptn）可有效调节钴（III）配合物[Co（eDDA）（ 2 R，4 R -ptn）] +（eDDA ＝乙二胺-N，N′-二乙酸酯）。该产品比Λ-对称-顺式：Δ-对称-顺式是3:97。立体选择性是出乎意料的高与，对于类似的复杂涉及（1比较- [R ），（2 - [R ）-环己烷-1,2-二胺（[R ，- [R -chxn），Λ-对称-顺：Δ-对称-顺式= 60:40。它是根据对两个顺式-[Co（eDDA）（2 R，4 R -ptn）] +的非对映异构体的晶体结构确定进行讨论的。在2的六元螯合环中观察到一个显着区别- [R，4 - [R -ptn其采用在Λ-对称-椅型构象顺式- [CO（EDDA）（2 - [R，4 - [R -ptn）] CLO 4 · ħ 2 Ó 1A但在Δ-对称-的λ歪斜船式构象顺式- [CO（EDDA）（2
• Preparation and Absorption and Circular Dichroism Spectra of Cobalt(III) Complexes with<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetrakis(2-aminoethyl)-1,2-ethanediamine, -1,3-propanediamine, -1,4-butanediamine, and -(<i>R</i>,<i>R</i>)-and -(<i>R</i>,<i>S</i>)- 2,4-pentanediamine
  作者：Kazumasa Hata、Myung-Ki Doh、Kazuo Kashiwabara、Junnosuke Fujita

  DOI：10.1246/bcsj.54.190

  日期：1981.1

  Cobalt(III) complexes of new sexidentate ligands,N,N,N′,N′-tetrakis(2-aminoethyl)-1,3-propanediamine (ttn), -1,4-butanediamine (ttmd), and -(R,R)- and -(R,S)-2,4-pentanediamine (tptn) were prepared and resolved except the RR-tptn complex which formed the Δ-isomer stereoselectively. The monocyano complexes of N,N,N′,N′-tetrakis(2-aminoethyl)-1,2-ethanediamine (ten) and ttn, in which the ligands act

  新的六齿配体的钴 (III) 配合物，N,N,N',N'-四(2-氨基乙基)-1,3-丙二胺 (ttn)、-1,4-丁二胺 (ttmd) 和 -(R ,R)- 和 -(R,S)-2,4-戊二胺 (tptn) 被制备和分离，除了 RR-tptn 复合物以立体选择性形成 Δ-异构体。还制备了 N,N,N',N'-四(2-氨基乙基)-1,2-乙二胺 (10) 和 ttn 的单氰基配合物，其中配体作为五分之一。将这些配合物和已知的 [Co(ten)]3+ 配合物的吸收光谱和 CD 光谱相互比较。六齿配合物的第一个 dd 吸收带，[Co(A)]3+ 按顺序移动到较小的波数，A 的 ttn>ten>ttmd，但 [Co(CN)(HA)]3+是相反的顺序，十> ttn。
• Ozaki, Shigeko; Mimura, Hisashi; Yasuhara, Naoko, Journal of the Chemical Society. Perkin transactions II, 1990, # 3, p. 353 - 360
  作者：Ozaki, Shigeko、Mimura, Hisashi、Yasuhara, Naoko、Masui, Masaichiro、Yamagata, Yuriko、et al.

  DOI：——

  日期：——
• Preparation, characterization, cytotoxicity, and mutagenicity of a pair of enantiomeric platinum(II) complexes with the potential to bind enantioselectively to DNA
  作者：Kymberley Vickery、Antonio M. Bonin、Ronald R. Fenton、Shaun O'Mara、Pamela J. Russell、Lorraine K. Webster、Trevor W. Hambley

  DOI：10.1021/jm00075a022

  日期：1993.11

  The synthesis of a pair of enantiomeric Pt(II) complexes, [Pt(RR-eaP)Cl2] and [Pt(S,S-eap)Cl2] (eap = N,N-diethyl-2,4-pentanediamine), designed to bind enantioselectively to GpG and ApG sequences of DNA is described. The in vitro cytotoxicity of each of the enantiomers toward murine leukemia and human bladder tumor cells has been measured. The RR enantiomer was found to be more active in the leukemia cells, but the difference was not as great as expected (IC50; R,R 14 muM, S,S 33 muM). In the bladder tumor cell line, no significant difference in activity was found. The two enantiomers had similar mutagenicity in the Salmonella reversion assay, but the R,R enantiomer was more cytotoxic in the bacterial cells. A structural analysis of the R,R enantiomer revealed that the ligand adopted an unexpected configuration, and a strain energy minimization analysis showed that this was a consequence of interactions between the diamine ligand and the dichloro ligands. The significance of the structural preferences with respect to the lower than expected enantiospecificity is discussed. Crystals of [Pt(RR-eap)Cl2] are monoclinic; space group, P2(1)2(1)2(1); a = 7.909(5), b = 12.972(9), and c = 13.269(12) angstrom; Z = 4; and the structure was refined to R = 0.025 (1657F).